GB816857A - Resolution of racemic aminoalcohols - Google Patents
Resolution of racemic aminoalcoholsInfo
- Publication number
- GB816857A GB816857A GB21715/54A GB2171554A GB816857A GB 816857 A GB816857 A GB 816857A GB 21715/54 A GB21715/54 A GB 21715/54A GB 2171554 A GB2171554 A GB 2171554A GB 816857 A GB816857 A GB 816857A
- Authority
- GB
- United Kingdom
- Prior art keywords
- base
- resolution
- precipitation
- racemic
- precipitated
- 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
Links
- 150000001414 amino alcohols Chemical class 0.000 title abstract 3
- 239000002585 base Substances 0.000 abstract 6
- 238000001556 precipitation Methods 0.000 abstract 5
- 150000003839 salts Chemical class 0.000 abstract 4
- 239000011780 sodium chloride Substances 0.000 abstract 4
- 238000000034 method Methods 0.000 abstract 3
- 238000001640 fractional crystallisation Methods 0.000 abstract 2
- 239000000463 material Substances 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 abstract 1
- FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 abstract 1
- 229960002748 Norepinephrine Drugs 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 1
- 239000012458 free base Substances 0.000 abstract 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- 229940095064 tartrate Drugs 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/10—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B57/00—Separation of optically-active compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A process for the resolution of diastereoisomeric salts of optically-active aminoalcohols comprises adding an alkaline material to a solution of the salts to effect fractional precipitation of the free base, one of the amino-alcohols being more readily precipitated than its stereo isomer and being present in the initial solution in a greater amount than that of the said stereo isomer, the amount of base precipitated being not substantially greater than the amount of said one amino alcohol in the initial solution. The fractional precipitation may be repeated by taking up the precipitated base in a suitable acid, such as d-tartaric or oxalic and again adding the alkaline material. The precipitation may be effected by the use of a mild base such as ammonia. The initial enrichment of the mixture in the desired optically active component can be effected by fractional crystallization or by adding to the racemic mixture a salt of the separated base from a preceding resolution. Examples describe the resolution of racemic adrenaline and of racemic noradrenaline to produce the laevo bases. After the first precipitation, either a second precipitation process or a fractional crystallization of the tartrate is carried out. The mother liquors contain predominantly the dextro base or a salt thereof which is racemized, and the racemate is reintroduced into the resolution process.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB816857A true GB816857A (en) | 1959-07-22 |
Family
ID=1736403
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB21715/54A Expired GB816857A (en) | 1954-07-26 | Resolution of racemic aminoalcohols |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB816857A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4111951A (en) * | 1977-01-17 | 1978-09-05 | Hoffmann-La Roche Inc. | Process for L-3,4-dehydroproline |
| CN116410096A (en) * | 2023-02-23 | 2023-07-11 | 河北广祥制药有限公司 | Preparation method of norepinephrine bitartrate |
-
1954
- 1954-07-26 GB GB21715/54A patent/GB816857A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4111951A (en) * | 1977-01-17 | 1978-09-05 | Hoffmann-La Roche Inc. | Process for L-3,4-dehydroproline |
| CN116410096A (en) * | 2023-02-23 | 2023-07-11 | 河北广祥制药有限公司 | Preparation method of norepinephrine bitartrate |
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