ES359765A1 - A PROCEDURE FOR THE PREPARATION OF 13 BETA-ETHYL-17 AL-FA - ETHINYL-17-HIDROXIGON-4-EN-3-ONA. - Google Patents

A PROCEDURE FOR THE PREPARATION OF 13 BETA-ETHYL-17 AL-FA - ETHINYL-17-HIDROXIGON-4-EN-3-ONA.

Info

Publication number
ES359765A1
ES359765A1 ES359765A ES359765A ES359765A1 ES 359765 A1 ES359765 A1 ES 359765A1 ES 359765 A ES359765 A ES 359765A ES 359765 A ES359765 A ES 359765A ES 359765 A1 ES359765 A1 ES 359765A1
Authority
ES
Spain
Prior art keywords
ethyl
butoxy
dione
pentyl
benzopyran
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
ES359765A
Other languages
Spanish (es)
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of ES359765A1 publication Critical patent/ES359765A1/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D315/00—Heterocyclic compounds containing rings having one oxygen atom as the only ring hetero atom according to more than one of groups C07D303/00 - C07D313/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/04—Saturated ethers
    • C07C43/12—Saturated ethers containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/64—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
    • C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D309/10—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D309/30—Oxygen atoms, e.g. delta-lactones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C07D311/92—Naphthopyrans; Hydrogenated naphthopyrans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/94—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/16—Radicals substituted by halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/26—Radicals substituted by doubly bound oxygen or sulfur atoms or by two such atoms singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/74—Naphthothiophenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/16—Benz[e]indenes; Hydrogenated benz[e]indenes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Steroid Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises 10-(3-oxobutyl)- 18 - methyl - 19 - nor - des - A - androstane - 5,17 - dione (I), its cyclization to 13# - ethyl - gon - 4 - ene - 3,17 - dione, and the conversion of this by treatment with an alkali metal acetylide or an acetylene magnesium halide in the presence of liquid ammonia to 13# - ethyl - 17[alpha] - ethynyl - 17# - hydroxy - gon-4-en-3-one, all these compounds being optically active or racemic. Compound I is prepared from 6-(4-tbutoxypentyl) - 2 - tetrahydropyranol (II) by the sequence II # 3,7-dihydroxy-11-t-butoxydodec-1-ene # 2-(2-diethylaminoethyl)-6-(4-tbutoxypentyl) - 2 - tetrahydropyranol # 3 - (4- t - butoxy - pentyl) - 6a# - ethyl - 2,3,5,6,6a,8 - hexahydro - cyclopenta[f][l] - benzopyran - 7(1H) - one # 3 - (4 - t - butoxy - pentyl) - 6a# - ethyl - 2,3,5,6,6a,8 - hexahydro - cyclopenta[f][l]- benzopyran - 7(1H) - ol # 6a,9a - trans - 3 - (4 - t - butoxy - pentyl) - 6a# - ethyl - 2,3,5,6,6a,- 8,9,9a - octahydro - cyclopenta[f][l]benzopyran- 7(1H) - ol # a mixture of 6a,9a - trans - 3 - (t - butoxy - pentyl) - 6a# - ethyl - perhydrocyclopenta[f][l]benzopyran - 4a,7 - diol and 3a,7a - trans - 4 - (7 - t - butoxy - 3 - hydroxyoctyl) - 7a# - ethyl - perhydro ndane - 1,5 - dione # 3a,7atrans - 4 - (7 - t - butoxy - 3 - oxo - octyl) - 7a# - ethyl - perhydroindane - 1,5 - dione # 10 - (3 - t - butoxy - butyl) - 18 - methyl - 19 - nor - des - A - androst - 9 - ene - 5,17 - dione # 10 - (3 - t - butoxybutyl) - 18 - methyl - 19 - nor - des - A - androstane - 5,17 - dione # 6a,9a - trans - 2 - methyl - 6a# - ethyl - 7 - oxo - perhydrocyclopenta[5,6]- naphtho[2,1-b]pyran - 11a - ol # I. 6 - (4 - t - Butoxy - pentyl) - 2 - tetrahydropyranol is prepared (a) from 6-(4 - t - butoxy - pentyl)-valerolactone or (b) from 5-chloro-2- pentanone via 5-chloro-2-pentanol and 5-chloro- 2-t-butoxy-pentane. Specification 1,207,048 is referred to.
ES359765A 1967-11-02 1968-10-31 A PROCEDURE FOR THE PREPARATION OF 13 BETA-ETHYL-17 AL-FA - ETHINYL-17-HIDROXIGON-4-EN-3-ONA. Expired ES359765A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US67998967A 1967-11-02 1967-11-02

Publications (1)

Publication Number Publication Date
ES359765A1 true ES359765A1 (en) 1970-06-16

Family

ID=24729197

Family Applications (1)

Application Number Title Priority Date Filing Date
ES359765A Expired ES359765A1 (en) 1967-11-02 1968-10-31 A PROCEDURE FOR THE PREPARATION OF 13 BETA-ETHYL-17 AL-FA - ETHINYL-17-HIDROXIGON-4-EN-3-ONA.

Country Status (11)

Country Link
BE (2) BE723188A (en)
BR (1) BR6803655D0 (en)
CH (2) CH503050A (en)
DE (2) DE1804796A1 (en)
DK (1) DK126041B (en)
ES (1) ES359765A1 (en)
FR (2) FR1586571A (en)
GB (2) GB1207048A (en)
IL (1) IL30982A0 (en)
NL (3) NL6815381A (en)
SE (2) SE356297B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH568336A5 (en) * 1969-04-04 1975-10-31 Hoffmann La Roche

Also Published As

Publication number Publication date
DE1804796A1 (en) 1969-06-26
DE1806410A1 (en) 1969-06-19
BR6803655D0 (en) 1973-03-15
BE723187A (en) 1969-04-30
NL6815622A (en) 1969-05-06
SE356297B (en) 1973-05-21
GB1207048A (en) 1970-09-30
SE355804B (en) 1973-05-07
DK126041B (en) 1973-06-04
CH503050A (en) 1971-02-15
IL30982A0 (en) 1969-01-29
NL6815381A (en) 1969-05-06
BE723188A (en) 1969-04-30
FR1590470A (en) 1970-04-13
FR1586571A (en) 1970-02-20
GB1207047A (en) 1970-09-30
CH503713A (en) 1971-02-28
NL6815555A (en) 1969-05-06

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