benzyl N-[1-(hydroxymethyl)cyclohexyl]carbamate → (1-Aminocyclohexyl)methanol

HRID 276251

Reaction equation

HRID 276251 reaction equation
C(OC([NH:11][C:12]1([CH2:18][OH:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=O)C1C=CC=CC=1>CO.[Pd]>[NH2:11][C:12]1([CH2:18][OH:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 1

HCID 18316421benzyl N-[1-(hydroxymethyl)cyclohexyl]carbamate

Product 1

HCID 409153(1-Aminocyclohexyl)methanol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A slurry of 1-(benzyloxycarbonylamino)-1-(hydroxymethyl)cyclohexane (4.0 g, 15 mmol) and 10% Pd/C (0.40 g) in MeOH (75 ml) was stirred under H2 (1 atm.) for 1 h, then treated with Celite®. The resulting mixture was filtered and concentrated under reduced pressure to give 1-amino-1-(hydroxymethyl)cyclohexane.

Workup

  1. additiontreated with Celite®
  2. filtrationThe resulting mixture was filtered
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b96e79cfef164e66b54433207daa4f14
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Linked notes

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