Carbamic acid, [1-(methoxymethyl)cyclopentyl]-, phenylmethyl ester → Cyclopentanamine, 1-(methoxymethyl)- (9CI)

HRID 1293397Notes

Reaction equation

HRID 1293397 reaction equation
C(OC(=O)[NH:10][C:11]1([CH2:16][O:17][CH3:18])[CH2:15][CH2:14][CH2:13][CH2:12]1)C1C=CC=CC=1>CO.[Pd]>[CH3:18][O:17][CH2:16][C:11]1([NH2:10])[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

4

Reactant 1

HCID 66756538Carbamic acid, [1-(methoxymethyl)cyclopentyl]-, phenylmethyl ester

Product 1

HCID 25220851Cyclopentanamine, 1-(methoxymethyl)- (9CI)

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of (1-methoxymethyl-cyclopentyl)-carbamic acid benzyl ester (150 mg, 0.57 mmol) in MeOH (5 mL) was added HCO2NH4 (216 mg, 3.42 mmol), followed by Pd/C (10%, 6 mg, 0.057 mmol). The resulting mixture was heated, to 70° C., for 2 hours. The reaction mixture was filtered and concentrated to provide the titled compound. MS (DCI) m/e 130 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-c70f078938544c35a6f8b9c8af8614ca
Source dataset
uspto-grants-2007_07
Patent number
US07238724B2

Reaction notes

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