HCID 178526628, compound → HCID 178507586, compound

HRID 724097Notes

Reaction equation

HRID 724097 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-5d9973f27b124747bb3500cdc281d237
Source dataset
uspto-grants-2006_11
Patent number
US07141580B2

Reaction notes

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