[(R)-1-Hydroxymethyl-3-(4-hydroxy-3-nitro-phenyl)-1-methyl-propyl]-carbamic acid tert-butyl ester → [(R)-3-(3-Amino-4-hydroxy-phenyl)-1-hydroxymethyl-1-methyl-propyl]-carbamic acid tert-butyl ester

HRID 1170409Notes

Reaction equation

HRID 1170409 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][C@:8]([CH2:22][OH:23])([CH3:21])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([N+:18]([O-])=O)[CH:12]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:24])[NH:7][C@:8]([CH2:22][OH:23])([CH3:21])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([NH2:18])[CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 68769414[(R)-1-Hydroxymethyl-3-(4-hydroxy-3-nitro-phenyl)-1-methyl-propyl]-carbamic acid tert-butyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 68768961[(R)-3-(3-Amino-4-hydroxy-phenyl)-1-hydroxymethyl-1-methyl-propyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

An argon purged solution of [(R)-1-Hydroxymethyl-3-(4-hydroxy-3-nitro-phenyl)-1-methyl-propyl]-carbamic acid tert-butyl ester (3.02 g, 8.87 mmol) in ethanol (40 ml) was treated with 10% Pd on activated charcoal (0.5 g). Argon was replaced by hydrogen and the reaction was allowed to proceed under atmospheric pressure for 2 hours. The reaction suspension was filtered and the filtrate evaporated to dryness in vacuum. Silica gel chromatography (eluent: DCM/methanol 20/1 to 10/1) followed by crystallization from diethyl ether provided the title compound as colorless crystals. mp 122.1/123.0° C.

Workup

  1. filtrationThe reaction suspension was filtered
  2. customthe filtrate evaporated to dryness in vacuum
  3. customSilica gel chromatography (eluent: DCM/methanol 20/1 to 10/1) followed by crystallization from diethyl ether

Sources & evidence

ORD record
ord-62e35946995342a09dd91459d028d52c
Source dataset
uspto-grants-2010_11
Patent number
US07825260B2

Reaction notes

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