NADP nicotinamide-adenine-dinucleotide phosphate → (S)-5-(4-Fluoro-phenyl)-5-hydroxy-1morpholin-4-yl-pentan-1-one

Participants

Role	Name	HCID	Charge
Reactant	NADP nicotinamide-adenine-dinucleotide phosphate	HCID 5886	—
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal	HCID 107526	—
Reactant	1-(4-Fluorophenyl)-5-(morpholin-4-yl)pentane-1,5-dione	HCID 58070809	—
Solvent	Methanol	HCID 887	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	(S)-5-(4-Fluoro-phenyl)-5-hydroxy-1morpholin-4-yl-pentan-1-one	HCID 23636213	—

Reaction Conditions

Temperature	31 °C

Reaction Steps

ES-KRED-119 (3.5 gm, Chiral Vision) was dissolved in 450 ml buffer (containing 250 mM potassium phosphate, 2 gm NADP+, 330 mM D-glucose, 1 gm glucose dehydrogenase, pH 7.0). A solution of 1-(4-Fluoro-phenyl)-5-morpholin-4-yl-pentane-1,5-dione in MeOH (50 gm in 50 ml) was added. The mixture was stirred at 31° C. for 24 hrs and monitored by HPLC. Ethyl acetate (250 ml) was added and the phases were separated. The organic layer was evaporated to get 49 gms of the (S)-5-(4-Fluoro-phenyl)-5-hydroxy-1morpholin-4-yl-pentan-1-one (ee: >99%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09388440B2
Source dataset	uspto-grants-2016_07
ORD ID	ord-8b649ac295624ea39c7d967283b07836
Source note	uspto-grants-2016_07