Ammonium formate → 4-Amino-4-methyl-cyclohexanol

HRID 1642699Notes

Reaction equation

HRID 1642699 reaction equation
C(OC(=O)[NH:10][C:11]1([CH3:18])[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].C(O)(C)C>[NH2:10][C:11]1([CH3:18])[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 66756996benzyl N-(4-hydroxy-1-methylcyclohexyl)carbamate

Product 1

HCID 223798474-Amino-4-methyl-cyclohexanol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of example 45E (169 mg, 0.64 mmol), ammonium formate (105 mg, 1.67 mmol) and 10% palladium on carbon (7 mg) in isopropanol (5 mL) was heated at 80° C. for 1 hour. The reaction mixture was cooled and filtered through a plug of Celite. The filter pad was washed with ethyl acetate (50 mL), and the filtrate was concentrated in vacuo to afford the titled compound as an inseparable mixture of diastereomers. MS (CI) m/z 130 (M+1)+; 1H NMR (300 MHz, CDCl3) δ ppm 3.77-3.71 (m, 2H), 3.65-3.61 (m, 2H), 1.87-1.61 (m, 4H), 1.63-1.33 (m, 10H), 1.15 (s, 3H), 1.11 (s, 3H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered through a plug of Celite
  3. washThe filter pad was washed with ethyl acetate (50 mL)
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-94368e3ca2dd4bba8c6fa82a6b441a03
Source dataset
uspto-grants-2012_02
Patent number
US08119664B2

Reaction notes

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