Tetrahydrofuran → tert-butyl [(1R,2R)-2-hydroxy-1-(3,4,5-trifluorophenyl)propyl]carbamate

HRID 1436108Notes

Reaction equation

HRID 1436108 reaction equation
C(=O)([O-])[O-].[K+].[K+].[N+](C1C=CC(C([O:16][C@H:17]([CH3:36])[C@H:18]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C:19]2[CH:24]=[C:23]([F:25])[C:22]([F:26])=[C:21]([F:27])[CH:20]=2)=O)=CC=1)([O-])=O.C1COCC1.C(OCC)(=O)C>CO>[OH:16][C@H:17]([CH3:36])[C@H:18]([NH:28][C:29](=[O:30])[O:31][C:32]([CH3:34])([CH3:33])[CH3:35])[C:19]1[CH:24]=[C:23]([F:25])[C:22]([F:26])=[C:21]([F:27])[CH:20]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 68911294[(1R,2R)-2-tert-butoxycarbonylamino-1-methyl-2-(3,4,5-trifluorophenyl)ethyl]4-nitrobenzoate

Product 1

HCID 68717986tert-butyl [(1R,2R)-2-hydroxy-1-(3,4,5-trifluorophenyl)propyl]carbamateYield 95.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate powder (6.43 g) was added to a mixed solution of (1R,2R)-2-tert-butoxycarbonylamino-1-methyl-2-(3,4,5-trifluorophenyl)ethyl 4-nitrobenzoate (7.03 g) in methanol (90 ml)-THF (10 ml), and the reaction solution was stirred at room temperature for one hour. Ethyl acetate was added to the reaction solution, which was then sequentially washed with water and brine (twice). The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Diethyl ether was added to the resulting residue, and the insoluble matter was removed by filtration. The filtrate was concentrated, and the resulting residue was purified by silica gel column chromatography (toluene:ethyl acetate=6:1) to obtain 4.49 g of the title compound.

Workup

  1. washwas then sequentially washed with water and brine (twice)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. additionDiethyl ether was added to the resulting residue
  5. customthe insoluble matter was removed by filtration
  6. concentrationThe filtrate was concentrated
  7. customthe resulting residue was purified by silica gel column chromatography (toluene:ethyl acetate=6:1)

Sources & evidence

ORD record
ord-311ea2cff9854063818b6afc119085dd
Source dataset
uspto-grants-2009_11
Patent number
US07618960B2

Reaction notes

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