Ethyl 3-(4-nitrobenzyl)cyclobutanecarboxylate → Ethyl 3-(4-aminobenzyl)cyclobutanecarboxylate

HRID 1713858Notes

Reaction equation

HRID 1713858 reaction equation
[N+:1]([C:4]1[CH:19]=[CH:18][C:7]([CH2:8][CH:9]2[CH2:12][CH:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:10]2)=[CH:6][CH:5]=1)([O-])=O>CCOC(C)=O>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][CH:9]2[CH2:10][CH:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:12]2)=[CH:18][CH:19]=1

Participants

3

Reactant 1

HCID 59464076Ethyl 3-(4-nitrobenzyl)cyclobutanecarboxylate

Product 1

HCID 59464168Ethyl 3-(4-aminobenzyl)cyclobutanecarboxylateYield 50%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 3-(4-nitrobenzyl)cyclobutanecarboxylate (4.02 mmol) was stirred in EtOAc (20 mL) at room temperature and nitrogen was bubbled through. 10% Palladium on carbon (160 mg) was added and the reaction vessel was put under an atmosphere of hydrogen. The mixture was stirred overnight then filtered through diatomaceous earth and concentrated by evaporation under reduced pressure. The residue was purified by chromatography eluting with 0-55% EtOAc/isohexane to give the title compound (466 mg, 50%) as an oil; 1H NMR δ 1.15-1.20 (3H, m), 1.77-1.94 (2H, m), 2.13-2.20 (2H, m), 2.33-2.37 (2H, m), 2.43-2.46 (1H, m), 2.53-2.56 (1H, m), 2.92-3.07 (1H, m), 4.01-4.08 (2H, m), 4.77 (2H, d), 6.46-6.49 (2H, m), 6.78-6.82 (2H, m); MS m/e M+MeCN 275.

Workup

  1. customnitrogen was bubbled through
  2. addition10% Palladium on carbon (160 mg) was added
  3. filtrationthen filtered through diatomaceous earth
  4. concentrationconcentrated by evaporation under reduced pressure
  5. customThe residue was purified by chromatography
  6. washeluting with 0-55% EtOAc/isohexane

Sources & evidence

ORD record
ord-b4d0eb53e10742b894d5f1644f5efc1b
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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