Reaction #6696

ord-9738564159bc4fc6bc633e268b9088a2

Reaction equation

COc1ccc(CC(C)=O)cc1OC
3,4-dimethoxyphenylacetone
NC(=O)C1=CN([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n4cnc5c(N)ncnc54)[C@H](OP(=O)(O)O)[C@@H]3O)[C@@H](O)[C@H]2O)C=CC1
NADPH
NC(=O)C1=CN([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n4cnc5c(N)ncnc54)[C@H](OP(=O)(O)O)[C@@H]3O)[C@@H](O)[C@H]2O)C=CC1
NADPH
→
COc1ccc(C[C@H](C)O)cc1OC
(S)-1-(3,4-dimethoxyphenyl)-2-propanol

Reactants

COc1ccc(CC(C)=O)cc1OC
3,4-dimethoxyphenylacetone
—
carbonyl
NC(=O)C1=CN([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n4cnc5c(N)ncnc54)[C@H](OP(=O)(O)O)[C@@H]3O)[C@@H](O)[C@H]2O)C=CC1
NADPH
NC(=O)C1=CN([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n4cnc5c(N)ncnc54)[C@H](OP(=O)(O)O)[C@@H]3O)[C@@H](O)[C@H]2O)C=CC1
NADPH
—
alcohol

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

The carbonyl reductases of the present invention can utilize NADPH as a coenzyme, have no alcohol dehydrogenating activity, and reduce 3,4-dimethoxyphenylacetone by utilizing NADPH as a coenzyme to produce 90% ee or more (S)-1-(3,4-dimethoxyphenyl)-2-propanol.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07083962B2uspto-grants-2006_08