t-butyl (1S)-2-(benzyloxy)-1-[(3-methylphenoxy)methyl]ethylcarbamate → t-butyl (1S)-2-hydroxy-1-[(3-methylphenoxy)methyl]ethylcarbamate

HRID 12409Notes

Reaction equation

HRID 12409 reaction equation
C([O:8][CH2:9][C@H:10]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=1)C1C=CC=CC=1>[C].[Pd].C(O)C>[OH:8][CH2:9][C@H:10]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:24])[CH3:26])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=1

Participants

4

Reactant 1

HCID 86761116t-butyl (1S)-2-(benzyloxy)-1-[(3-methylphenoxy)methyl]ethylcarbamate

Product 1

HCID 68697680t-butyl (1S)-2-hydroxy-1-[(3-methylphenoxy)methyl]ethylcarbamateYield 104.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To t-butyl (1S)-2-(benzyloxy)-1-[(3-methylphenoxy)methyl]ethylcarbamate (3.8 g) obtained in Step 2 of Example 15 were added 10% palladium-carbon (wet, 1 g) and ethanol (30 ml), and the mixture was stirred for 2 days under hydrogen atmosphere. After celite filtration, the solvent was evaporated. The obtained crude product was purified by silica gel chromatography (ethyl acetate-hexane) to give the title compound (3.0 g).

Workup

  1. filtrationAfter celite filtration
  2. customthe solvent was evaporated
  3. customThe obtained crude product
  4. customwas purified by silica gel chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-b75428cddf274b5f91f1a55d8afead7e
Source dataset
uspto-grants-2010_06
Patent number
US07728005B2

Reaction notes

Loading…