US4831185A
Expired / Lapsed
US
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Asymmetric synthesis of natural vitamin E
Assignee: Hoffmann La Roche Inc
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Filing: 1987-12-18
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Granted: 1989-05-16
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Expires: 2007-12-18
Abstract
Abstract A new approach to produce vitamin E in optically active pure form involving an asymmetric synthesis and novel intermediates therein.
Inventors
- 👤 Ka-Kong Chan
- 👤 Gabriel G. Saucy
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 19:37
CPC Classifications
C; C07; C07D; C07D311/00; C07D311/02; C07D311/04; C07D311/58; C07D311/70; C07D311/72; C07C; C07C46/00; C07C46/02; C07C46/06; C07C46/10; C07C50/00; C07C50/26; C07C50/28
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
108 words
A process of resolving a racemate of the formula: ##STR21## wherein R taken together with its attached oxygen atom forms a hydrolyzable ester protecting group and R 4 is phenyl or phenyl substituted which from 1 to 3 halo groups; into its two optical antipodes one of which has the formula: ##STR22## wherein R and R 4 are as above: and the other of which has the formula ##STR23## wherein R and R 4 are as above; comprising forming a solution by dissolving said racemate in an inert hydrocarbon solvent and crystallizing one of said antipodes from said solution while leaving the other of said antipodes in solution.
Claim 2
Dependent Claim
108 words
A process of resolving a racemate of the formula: ##STR21## wherein R taken together with its attached oxygen atom forms a hydrolyzable ester protecting group and R 4 is phenyl or phenyl substituted which from 1 to 3 halo groups; into its two optical antipodes one of which has the formula: ##STR22## wherein R and R 4 are as above: and the other of which has the formula ##STR23## wherein R and R 4 are as above; comprising forming a solution by dissolving said racemate in an inert hydrocarbon solvent and crystallizing one of said antipodes from said solution while leaving the other of said antipodes in solution.
Claim 3
Dependent Claim
24 words
The process of claim 1 wherein said solution is formed and said crystallization occurs at a temperature of from -25° C. to 30° C.
Claim 4
Dependent Claim
13 words
The process of claim 1 wherein said solvent is an aromatic hydrocarbon solvent.
Claim 5
Dependent Claim
32 words
The process of claim 3 wherein said crystallization is carried out by seeding said solution with at least one crystal of the optical antipode which is to be crystallized from said solution.
Claim 6
Dependent Claim
10 words
The process of claim 4 wherein said solvent is toluene.
Claim 7
Dependent Claim
54 words
An optically active antipode of the formula: ##STR24## wherein R taken together with its attached oxygen atom forms a hydrolyzable ester protecting group; R 7 is hydrogen, ##STR25## and R 8 is phenyl or phenyl substituted with from 1 to 3 halo groups. said antipode being substantially free of its other optically active antipodes.
Claim 8
Dependent Claim
54 words
An optically active antipode of the formula: ##STR24## wherein R taken together with its attached oxygen atom forms a hydrolyzable ester protecting group; R 7 is hydrogen, ##STR25## and R 8 is phenyl or phenyl substituted with from 1 to 3 halo groups. said antipode being substantially free of its other optically active antipodes.
Claim 9
Dependent Claim
10 words
The antipode of claim 6 wherein R 7 is hydrogen.
Claim 10
Dependent Claim
9 words
The antipode of claim 7 wherein R is acetyl.
Claim 11
Dependent Claim
10 words
The antipode of claim 6 wherein R 7 is ##STR26##
Claim 12
Dependent Claim
10 words
The antipode of claim 9 wherein R 8 is phenyl.
Claim 13
Dependent Claim
9 words
The antipode of claim 9 wherein R is acetyl.
Claim 14
Dependent Claim
54 words
An optically active antipode of the formula: ##STR27## wherein R taken together with its attached oxygen atom forms a hydrolyzable ester protecting group; R 7 is hydrogen, ##STR28## and R 8 is phenyl or phenyl substituted with from 1 to 3 halo groups said antipode being substantially free of its other optically active antipode.
Claim 15
Dependent Claim
54 words
An optically active antipode of the formula: ##STR27## wherein R taken together with its attached oxygen atom forms a hydrolyzable ester protecting group; R 7 is hydrogen, ##STR28## and R 8 is phenyl or phenyl substituted with from 1 to 3 halo groups said antipode being substantially free of its other optically active antipode.
Claim 16
Dependent Claim
10 words
The antipode of claim 12 wherein R 7 is hydrogen.
Claim 17
Dependent Claim
9 words
The antipode of claim 13 wherein R is acetyl.
Claim 18
Dependent Claim
10 words
The antipode of claim 12 wherein R 7 is ##STR29##
Claim 19
Dependent Claim
10 words
The antipode of claim 15 wherein R 8 is phenyl.
Claim 20
Dependent Claim
9 words
The antipode of claim 16 wherein R is acetyl.
References Cited (Backward Citations)
US4626276A
Cited
JPH01231005A
Cited
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