Methyl 1-(4-nitrophenyl)cyclobutylcarbamate → Methyl 1-(4-aminophenyl)cyclobutylcarbamate

HRID 1779087Notes

Reaction equation

HRID 1779087 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2([NH:14][C:15](=[O:18])[O:16][CH3:17])[CH2:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2([NH:14][C:15](=[O:18])[O:16][CH3:17])[CH2:11][CH2:12][CH2:13]2)=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 86712723Methyl 1-(4-nitrophenyl)cyclobutylcarbamate

Product 1

HCID 86712724Methyl 1-(4-aminophenyl)cyclobutylcarbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of Pd/C (10%) (120 mg) and methyl 1-(4-nitrophenyl)cyclobutylcarbamate (A118) (404 mg, 1.61 mmol) in MeOH (17.0 mL) was vigorously stirred overnight under a hydrogen atmosphere. The resulting mixture was filtered through Celite then the filtrate concentrated in vacuo. The residue was purified using silica gel column chromatography (CombiFlash Rf, SiO2 cartridge, 0-75% EtOAc in cyclohexane) to give the title compound A119 (237 mg, 67%); 1H NMR (300 MHz, CDCl3); δ 7.21 (d, J=8.3 Hz, 2H), 6.63 (d, J=8.5 Hz, 2H), 5.57 (brs, 1H), 3.66 (s, 2H), 3.58 (s, 3H), 2.48 (m, 4H), 2.02 (m, 1H), 1.80 (m, 1H). LCMS-B: rt 2.35 min; m/z 221.2 [M+H]+.

Workup

  1. filtrationThe resulting mixture was filtered through Celite
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe residue was purified

Sources & evidence

ORD record
ord-7754872793e845fea06f5ad37ff9d96c
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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