HCID 178526628, compound → HCID 178507586, compound

HRID 858455Notes

Reaction equation

HRID 858455 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C@H:10]2[CH2:13][C@H:12]([OH:14])[CH2:11]2)=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C@H:10]2[CH2:11][C@H:12]([OH:14])[CH2:13]2)=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 178526628HCID 178526628, compound

Product 1

HCID 178507586HCID 178507586, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of trans-3-(4-nitrophenyl)cyclobutanol (step 3, 1.0 g, 4.9 mmol) in methanol (20 mL) was added 10% Pd—C (50 mg). The mixture was stirred at room temperature under hydrogen atmosphere for 2.5 h. The palladium catalyst was removed by filtration and washed with methanol (100 mL) and ethyl acetate (100 mL). The filtrate was concentrated under reduced pressure to afford 0.9 g (quant.) of the title compound as pale yellow solids: MS (EI) m/z 163 (M+); 1H-NMR (CDCl3) δ 7.03 (2H, d, J=8.3 Hz), 6.66 (2H, d, J=8.3 Hz), 4.56–4.47 (1H, m), 3.58–3.48 (3H, m), 2.48–2.31 (2H, m), 1.73 (1H, d, J=5.1 Hz).

Workup

  1. customThe palladium catalyst was removed by filtration
  2. washwashed with methanol (100 mL) and ethyl acetate (100 mL)
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d143d62472d94e498a735516d924a0f3
Source dataset
uspto-grants-2006_12
Patent number
US07148234B2

Reaction notes

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