Methyl-(3-nitro-4-propyl-phenyl)-carbamic acid tert-butyl ester → (3-Amino-4-propyl-phenyl)-methyl-carbamic acid tert-butyl ester

HRID 401365Notes

Reaction equation

HRID 401365 reaction equation
[C:1]([O:5][C:6](=[O:21])[N:7]([CH3:20])[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH3:16])=[C:10]([N+:17]([O-])=O)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2]>CCOC(C)=O.[Pd]>[C:1]([O:5][C:6](=[O:21])[N:7]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH3:16])=[C:10]([NH2:17])[CH:9]=1)[CH3:20])([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 1

HCID 66676075Methyl-(3-nitro-4-propyl-phenyl)-carbamic acid tert-butyl ester

Product 1

HCID 66676102(3-Amino-4-propyl-phenyl)-methyl-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl-(3-nitro-4-propyl-phenyl)-carbamic acid tert-butyl ester (110 mg, 0.37 mmol) in EtOAc (10 ml) was added 10% Pd—C (100 mg). The resulting suspension was stirred at room temperature under H2 (1 atm) for 2 days. The progress of the reaction was monitored by TLC. Upon completion, the reaction mixture was filtered through a pad of Celite. The filtrate was concentrated in vacuo to afford (3-Amino-4-propyl-phenyl)-methyl-carbamic acid tert-butyl ester (D-15) as a colorless crystalline compound (80 mg, 81%). ESI-MS 265.3 m/z (MH+).

Workup

  1. filtrationUpon completion, the reaction mixture was filtered through a pad of Celite
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-7743d62663b64cf5a2a40a30ec5f6c6a
Source dataset
uspto-grants-2014_06
Patent number
US08741925B2

Reaction notes

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