(1R,2R)-N-tert-Butoxycarbonyl-2-benzyloxycyclohexylamine → (1R,2R)-trans-N-Boc-2-Aminocyclohexanol

HRID 1007287Notes

Reaction equation

HRID 1007287 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[O:15]CC1C=CC=CC=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[OH:15])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 59025417(1R,2R)-N-tert-Butoxycarbonyl-2-benzyloxycyclohexylamine

Product 1

HCID 10921888(1R,2R)-trans-N-Boc-2-AminocyclohexanolYield 94.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 3.0 g of (1R,2R)-N-tert-butoxycarbonyl-2-benzyloxycyclohexylamine in 100 mL of methanol was combined with 300 mg of 5% palladium on carbon, and hydrogenated at room temperature under atmospheric pressure. After 48 hours, palladium on carbon was filtered off, and the filtrate was concentrated. The residue was subjected to chromatography on silica gel (n-hexane:ethyl acetate 2:1) to obtain 2.0 g of the desirable compound.

Workup

  1. customhydrogenated at room temperature
  2. filtrationpalladium on carbon was filtered off
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-4b7f160bfd1f4e199760cdd4b48e093b
Source dataset
uspto-grants-2004_09
Patent number
US06794389B2

Reaction notes

Loading…