Ammonium Chloride → Tert-butyl 7-({[tert-butyl(dimethyl)silyl]oxy}methyl)-7-(3,4-dichlorophenyl)-6-hydroxy-1,4-oxazepane-4-carboxylate

HRID 1022830Notes

Reaction equation

HRID 1022830 reaction equation
[Si:1]([O:8][CH2:9][C:10]1([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=2)[O:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12][C:11]1=[O:24])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[BH4-].[Na+].[Cl-].[NH4+]>CO>[Si:1]([O:8][CH2:9][C:10]1([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=2)[O:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12][CH:11]1[OH:24])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 66975958Tert-butyl 7-({[tert-butyl(dimethyl)silyl]oxy}methyl)-7-(3,4-dichlorophenyl)-6-oxo-1,4-oxazepane-4-carboxylate

Product 1

HCID 66975347Tert-butyl 7-({[tert-butyl(dimethyl)silyl]oxy}methyl)-7-(3,4-dichlorophenyl)-6-hydroxy-1,4-oxazepane-4-carboxylateYield 22.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution (25 mL) of tert-butyl 7-({[tert-butyl(dimethyl)silyl]oxy}methyl)-7-(3,4-dichlorophenyl)-6-oxo-1,4-oxazepane-4-carboxylate (1.34 g) in methanol was added sodium borohydride (221 mg), and the mixture was stirred at room temperature for 1 hr. To the reaction solution was added saturated aqueous ammonium chloride, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (303 mg) as a high-polar diastereomer. In addition, a less polar diastereomer (836 mg) was isolated.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-45df27bb313f4a34b2cfdca2bf487dd5
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

Loading…