Stereoselective preparation of halophenyl alcohols from ketones
AssigneeE. R. Squibb & Sons, Inc.
InventorsRamesh N. Patel, Mark Liu, Amit Banerjee, Laszlo J. Szarka
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Abstract
A process is described for selectively preparing a compound of the formula ##STR1## wherein: R.sup.1 is halogen; R.sup.2 is halogen, alkyl, cycloalkyl, aryl or ##STR2## and R.sup.3 hydrogen, alkyl, cycloalkyl, aryl, ##STR3## wherein the process comprises treating the associated ketone with an oxido-reductase or a microorganism comprising an oxidoreductase. Compounds prepared by this process are useful antipsychotic agents or useful intermediates therefor.
Claims9
A process for selectively preparing an R- or S- isomer of a product of the formula ##STR13## wherein:
- R.sup.1 is halogen;
- R.sup.2 is ##STR14## and R.sup.3 is hydrogen, alkyl, cycloalkyl, aryl, or ##STR15## and wherein the process comprises:
- (a) treating a substrate of the formula ##STR16## wherein R.sup.1 and R.sup.2 have the same meaning as above with a microorganism selected from a group consisting of:
- Hansenula polymorpha ATCC 26012,
- Hansenula polymorpha ATCC 86014,
- Rhodococcus sp. ATCC 21243,
- Nocardia globerula ATCC 21505,
- Nocardia petroleophila ATCC 15776,
- Arthrobacter simplex ATCC 6949,
- Rhodococcus rhodochrous ATCC 29675,
- Mycobacterium vacca ATCC 29678,
- Hansenula anomala ATCC 36903,
- Candida boidini ATCC 32,195,
- Saccharomyces cerevisiae ATCC 60731,
- Rhodochococcus rhodochrous ATCC 13808,
- Pichia methanolica ATCC 56508,
- Pullalaria pullulans ATCC 16623,
- Trigonopsis variables ATCC 10679, and
- Cunninghamella echinalata ATCC 26269,
- or an oxidoreductase deriveable therefrom;
- and
- (b) recovering the optically active product therefrom.
A process for selectively preparing an R-isomer of the formula ##STR18## wherein:
- R.sup.1 is halogen;
- R.sup.2 is ##STR19## and R.sup.3 is hydrogen, alkyl, cycloalkyl, aryl, or ##STR20## and wherein the process comprises:
- (a) treating a substrate of the formula ##STR21## wherein R.sup.1 and R.sup.2 have the same meaning as above with a microorganism selected from a group consisting of:
- Arthrobacter simplex ATCC 6949,
- Candida boidini ATCC 32195,
- Hansenula anomala 36903,
- Hansenula polymorpha ATCC 26012 and 86014,
- Mycobacterium vacca ATCC 29678,
- Nocardia globerula ATCC 21505,
- Nocardia petroleophila ATCC 15776,
- Pullularia pullulans ATCC 16623,
- Rhodococcus sp. ATCC 21243,
- Rhodococcus rhodochrous ATCC 29675, and
- Saccharomyces cerevisiae ATCC 60731 or an oxido-reductase deriveable therefrom;
- and
- (b) recovering the optically active product therefrom.
A process for selectively preparing an S-isomer product of the formula ##STR23## wherein:
- R.sup.1 is halogen,
- R.sup.2 is halogen, alkyl, cycloalkyl, aryl or ##STR24## and R.sup.3 is hydrogen, alkyl, cycloalkyl, aryl, or ##STR25## and wherein the process comprises:
- (a) treating a substrate of the formula ##STR26## wherein R.sup.1 and R.sup.2 have the same meaning as above with a microorganism selected from:
- Rhodococcus rhodochrous ATCC 13808,
- Pichia methanolica ATCC 56508,
- Pullularia pullulans ATCC 16623,
- Trigonopsis variables ATCC 10679, and
- Cunninghamella echinalata ATCC 26269,
- or an oxido-reductase deriveable therefrom;
- and
- (b) recovering the optically active product therefrom.
A process for selectively preparing an R- or S- isomer of a product of the formula ##STR27## wherein:
- R.sup.1 is halogen;
- R.sup.2 is halogen, alkyl, cycloalkyl, aryl or ##STR28## and R.sup.3 is hydrogen, alkyl, cycloalkyl, aryl, or ##STR29## and wherein the process comprises:
- (a) treating a substrate of the formula ##STR30## wherein R.sup.1 and R.sup.2 have the same meaning as above with a microorganism selected from a group consisting of:
- Hansenula polymorpha ACTT 26012,
- Hansenula polymorpha ACTT 86014,
- Rhodococcus sp. ACTT 21243,
- Nocardia globerula ACTT 21505,
- Nocardia petroleophila ACTT 15776,
- Arthrobacter simplex ACTT 6949,
- Rhodococcus rhodochrous ACTT 29675,
- Mycobacterium vacca ACTT 29678,
- Candida boidini ACTT 32,195,
- Saccharomyces cerevisiae ACTT 60731,
- Rhodochococcus rhodochrous ACTT 13808,
- Pichia methanolica ACTT 56508,
- Pullularia pullulans ACTT 16623,
- Trigonopsis variables ACTT 10679, and
- Cunninghamella echinalata ACTT 26269, or an oxidoreductase deriveable therefrom;
- and
- (b) recovering the optically active product therefrom.
Dependencies are inferred from the claim text.