IE42206L - Optical resolution of 1-t-butylamino-2, 3-dihydroxypropane - Google Patents
Optical resolution of 1-t-butylamino-2, 3-dihydroxypropaneInfo
- Publication number
- IE42206L IE42206L IE752702A IE270275A IE42206L IE 42206 L IE42206 L IE 42206L IE 752702 A IE752702 A IE 752702A IE 270275 A IE270275 A IE 270275A IE 42206 L IE42206 L IE 42206L
- Authority
- IE
- Ireland
- Prior art keywords
- dihydroxypropane
- butylamino
- diastereoisomer
- solution
- optical resolution
- Prior art date
Links
- JWBMVCAZXJMSOX-UHFFFAOYSA-N 3-(tert-butylamino)propane-1,2-diol Chemical compound CC(C)(C)NCC(O)CO JWBMVCAZXJMSOX-UHFFFAOYSA-N 0.000 title abstract 5
- 230000003287 optical effect Effects 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 abstract 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 abstract 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 abstract 1
- ODHCTXKNWHHXJC-GSVOUGTGSA-N 5-oxo-D-proline Chemical compound OC(=O)[C@H]1CCC(=O)N1 ODHCTXKNWHHXJC-GSVOUGTGSA-N 0.000 abstract 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229960001270 d- tartaric acid Drugs 0.000 abstract 1
- 239000003456 ion exchange resin Substances 0.000 abstract 1
- 229920003303 ion-exchange polymer Polymers 0.000 abstract 1
- FEWJPZIEWOKRBE-LWMBPPNESA-N levotartaric acid Chemical compound OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
- C07C215/10—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic with one amino group and at least two hydroxy groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B53/00—Asymmetric syntheses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B57/00—Separation of optically-active compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1470030 Optical resolution of 1-t-butylamino- 2,3-dihydroxypropane MERCK & CO Inc 10 Dec 1975 [13 Dec 1974 25 Sept 1975] 50632/75 Heading C2C Mixtures of enantiomers of 1-t-butylamino- 2,3-dihydroxypropane are optically resolved by (1) treating a solution of the mixture with a resolving agent selected from S-pyroglutamic acid, R-pyroglutamic acid, L-tartaric acid and D-tartaric acid (2) separating from the solution the solid diastereoisomer which forms and (3) recovering from the diastereoisomer a single enantiomer of 1-t-butylamino-2,3-dihydroxypropane, e.g. by treating it with a base or running a solution of the diastereoisomer through an ion-exchange resin. The initial mixture of enantiomers of 1-t-butylamino-2,3-dihydroxypropane may be made by reacting t-butylamine with glycidol.
[GB1470030A]
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53254774A | 1974-12-13 | 1974-12-13 | |
| US61594175A | 1975-09-25 | 1975-09-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE42206L true IE42206L (en) | 1976-06-13 |
| IE42206B1 IE42206B1 (en) | 1980-06-18 |
Family
ID=27063872
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2702/75A IE42206B1 (en) | 1974-12-13 | 1975-12-11 | Optical resolution of 1-t-butylamino -2,3-dihydroxypropane |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS51118711A (en) |
| AU (1) | AU510799B2 (en) |
| CA (1) | CA1064943A (en) |
| DE (1) | DE2556040C2 (en) |
| DK (1) | DK532575A (en) |
| FR (2) | FR2294151A1 (en) |
| GB (1) | GB1470030A (en) |
| IE (1) | IE42206B1 (en) |
| NL (1) | NL7513818A (en) |
| SE (1) | SE435499B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5931693A (en) * | 1982-08-13 | 1984-02-20 | Kanegafuchi Chem Ind Co Ltd | Preparation of optical active oxazolidinone derivative |
| JPH01149775A (en) * | 1987-12-07 | 1989-06-12 | Kawaken Fine Chem Co Ltd | Production of optically active 2-methylpiperazine |
| US5684159A (en) * | 1995-05-30 | 1997-11-04 | Rhone-Poulenc Rorer S.A. | L-tartaric acid salt of a (1R) diastereomer of a 2-azadihydroxybicyclo 2.2.1!heptane compound and the preparation of 2-azabicyclo 2.2.1!heptane compounds |
| IN187238B (en) * | 1995-06-30 | 2002-03-09 | Astra Ab | |
| AU2017238859B2 (en) * | 2016-03-25 | 2021-02-18 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Crystal forms and methods of synthesis of (2R, 6R)-hydroxynorketamine and (2S, 6S)-hydroxynorketamine |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2528267A (en) * | 1950-10-31 | Eobeet j | ||
| US3116332A (en) * | 1958-10-17 | 1963-12-31 | Du Pont | Resolution of racemic aminoisopropanol |
-
1975
- 1975-11-26 DK DK532575A patent/DK532575A/en not_active Application Discontinuation
- 1975-11-26 NL NL7513818A patent/NL7513818A/en active Search and Examination
- 1975-11-26 SE SE7513307A patent/SE435499B/en not_active IP Right Cessation
- 1975-12-03 AU AU87220/75A patent/AU510799B2/en not_active Expired
- 1975-12-08 CA CA241,257A patent/CA1064943A/en not_active Expired
- 1975-12-09 FR FR7537575A patent/FR2294151A1/en active Granted
- 1975-12-10 GB GB5063275A patent/GB1470030A/en not_active Expired
- 1975-12-11 IE IE2702/75A patent/IE42206B1/en unknown
- 1975-12-12 JP JP50147481A patent/JPS51118711A/en active Pending
- 1975-12-12 DE DE2556040A patent/DE2556040C2/en not_active Expired
-
1976
- 1976-05-04 FR FR7613241A patent/FR2303790A1/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| SE7513307L (en) | 1976-06-14 |
| AU510799B2 (en) | 1980-07-17 |
| DE2556040C2 (en) | 1986-05-07 |
| FR2294151A1 (en) | 1976-07-09 |
| JPS51118711A (en) | 1976-10-18 |
| DK532575A (en) | 1976-06-14 |
| GB1470030A (en) | 1977-04-14 |
| DE2556040A1 (en) | 1976-06-16 |
| FR2294151B1 (en) | 1979-04-06 |
| SE435499B (en) | 1984-10-01 |
| IE42206B1 (en) | 1980-06-18 |
| FR2303790A1 (en) | 1976-10-08 |
| FR2303790B1 (en) | 1980-07-18 |
| AU8722075A (en) | 1977-06-09 |
| NL7513818A (en) | 1976-06-15 |
| CA1064943A (en) | 1979-10-23 |
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