(R)-2-(tert-butoxycarbonyl)amino-2-(4-benzyloxyphenyl)ethanol → (R)-tert-butyl (2-hydroxy-1-(4-hydroxyphenyl)ethyl)carbamate

HRID 454990Notes

Reaction equation

HRID 454990 reaction equation
[C:1]([O:5][C:6](=[O:25])[NH:7][C@H:8]([C:11]1[CH:16]=[CH:15][C:14]([O:17]CC2C=CC=CC=2)=[CH:13][CH:12]=1)[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2]>C(O)C.ClCCl.[Pd]>[C:1]([O:5][C:6](=[O:25])[NH:7][C@H:8]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)[CH2:9][OH:10])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 60086323(R)-2-(tert-butoxycarbonyl)amino-2-(4-benzyloxyphenyl)ethanol

Product 1

HCID 67073553(R)-tert-butyl (2-hydroxy-1-(4-hydroxyphenyl)ethyl)carbamateYield 91%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

[(R)-1-(4-Benzyloxy-phenyl)-2-hydroxy-ethyl]-carbamic acid t-butyl ester (2.013 g, 5.87 mmol) and 10% Palladium on active carbon (0.300 g, 0.294 mmol) were mixed in ethanol (15 ml) and dichloromethane (5 ml). The hydrogenation was carried at 1 atmosphere at room temperature overnight. The catalyst was filtered out. The filtrate was concentrated to a white solid (1.350 g, 91% yield): 1H NMR (400 MHz, MeOD) δ ppm 7.36 (d, 2H), 6.97 (m, 2H), 3.83 (m, 1H), 3.54 (dt, J=3.2, 1.5 Hz, 2 H), 1.66 (m, 9H); LCMS (ESI) m/e 254.1 [(M+H), calcd. for C13H20NO4 254.3].

Workup

  1. filtrationThe catalyst was filtered out

Sources & evidence

ORD record
ord-572efdd7bf3c48ec9b30f3c80352a130
Source dataset
uspto-grants-2013_07
Patent number
US08497271B2

Reaction notes

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