Water → HCID 20810218, compound

HRID 895111Notes

Reaction equation

HRID 895111 reaction equation
[F:1][C:2]([F:20])([C:16]([F:19])([F:18])[F:17])[CH2:3][N:4]=[C:5]1NC2C=CC=CC=2O[CH:6]1[CH3:15].[BH4-].[Na+].[OH2:23].[C:24]([O:27][CH2:28][CH3:29])(=O)[CH3:25]>CO>[CH3:25][C@@H:24]1[C:5](=[O:23])[NH:4][C:3]2[CH:2]=[C:6]([CH2:5][NH:4][CH2:3][C:2]([F:1])([F:20])[C:16]([F:17])([F:18])[F:19])[CH:15]=[CH:29][C:28]=2[O:27]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 137241971HCID 137241971, compound

Product 1

HCID 20810218HCID 20810218, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

712 mg (2.21 mmol) of (2R)-methyl-3-oxo-6-(2,2,3,3,3,-pentafluoropropylimino-methyl-3,4-dihydro-2H-1,4-benzoxazine is dissolved in 30 ml of methanol and mixed with 83.6 mg (2.21 mmol) of sodium borohydride. After stirring overnight at room temperature, the batch is added to water and shaken three times with ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution, dried and spun in. After chromatography on silica gel (mobile solvent: ethyl acetate/hexane), 396.7 mg (55%) of the desired compound is obtained.

Workup

  1. washThe combined organic phases are washed with saturated sodium chloride solution
  2. customdried

Sources & evidence

ORD record
ord-5bfa766be04a4e3a912a1345a442a2b4
Source dataset
uspto-grants-2005_07
Patent number
US06914059B2

Reaction notes

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