tert-butyl N-[2-(2-benzyloxy-4-isopropylphenyl)ethyl]carbamate → tert-butyl N-[2-(2-hydroxy-4-isopropylphenyl)ethyl]carbamate

HRID 229577Notes

Reaction equation

HRID 229577 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([CH:15]([CH3:17])[CH3:16])[CH:12]=[CH:11][C:10]=1[CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])C1C=CC=CC=1>C(O)C.[Pd]>[OH:8][C:9]1[CH:14]=[C:13]([CH:15]([CH3:16])[CH3:17])[CH:12]=[CH:11][C:10]=1[CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:26])[CH3:25]

Participants

4

Reactant 1

HCID 18457007tert-butyl N-[2-(2-benzyloxy-4-isopropylphenyl)ethyl]carbamate

Product 1

HCID 18457008tert-butyl N-[2-(2-hydroxy-4-isopropylphenyl)ethyl]carbamateYield 73.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

tert-Butyl N-[2-(2-benzyloxy-4-isopropylphenyl)ethyl]carbamate (12.00 g) was dissolved in 150 mL of ethanol. To the stirred solution was added 1.10 g of 10% palladium on carbon under ice-cooling, and the mixture was stirred under a hydrogen atmosphere and ordinary pressure at 30° C. for 16 hours. The insoluble material was filtered, and the filtrate was concentrated under reduced pressure to give 6.66 g of tert-butyl N-[2-(2-hydroxy-4-isopropylphenyl)ethyl]carbamate.

Workup

  1. temperaturecooling
  2. filtrationThe insoluble material was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-74a6a00d2a3144e99f36c16b5b490781
Source dataset
uspto-grants-2009_07
Patent number
US07563822B2

Reaction notes

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