NADP nicotinamide-adenine-dinucleotide phosphate → (S)-5-(4-Fluoro-phenyl)-5-hydroxy-1morpholin-4-yl-pentan-1-one
Reaction equation
P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1C=[N+]([C@@H]2O[C@H](COP(OP(OC[C@H]3O[C@@H](N4C5N=CN=C(N)C=5N=C4)[C@H](OP(O)(O)=O)[C@@H]3O)(O)=O)(O)=O)[C@@H](O)[C@H]2O)C=C(C(N)=O)C=1.O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.[F:69][C:70]1[CH:75]=[CH:74][C:73]([C:76](=[O:88])[CH2:77][CH2:78][CH2:79][C:80]([N:82]2[CH2:87][CH2:86][O:85][CH2:84][CH2:83]2)=[O:81])=[CH:72][CH:71]=1>CO.C(OCC)(=O)C>[F:69][C:70]1[CH:75]=[CH:74][C:73]([C@@H:76]([OH:88])[CH2:77][CH2:78][CH2:79][C:80]([N:82]2[CH2:83][CH2:84][O:85][CH2:86][CH2:87]2)=[O:81])=[CH:72][CH:71]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 31 °C
Procedure
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%).
Workup
- customthe phases were separated
- customThe organic layer was evaporated
Sources & evidence
- ORD record
- ord-8b649ac295624ea39c7d967283b07836
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09388440B2
Reaction notes
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