HCID 178471530, compound → HCID 178471529, compound

HRID 1713870Notes

Reaction equation

HRID 1713870 reaction equation
C1(C(=[N:14][C:15]2[CH:20]=[CH:19][C:18]([C@H:21]3[CH2:26][CH2:25][C@H:24]([CH:27]([CH3:33])[C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:23][CH2:22]3)=[CH:17][CH:16]=2)C2C=CC=CC=2)C=CC=CC=1>[Pd].C(O)C>[NH2:14][C:15]1[CH:16]=[CH:17][C:18]([C@H:21]2[CH2:22][CH2:23][C@H:24]([CH:27]([CH3:33])[C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:25][CH2:26]2)=[CH:19][CH:20]=1

Participants

4

Reactant 1

HCID 178471530HCID 178471530, compound

Product 1

HCID 178471529HCID 178471529, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Palladium on carbon (500 mg) was added in one portion to a stirred solution of trans-ethyl 2-(4-{4-[(diphenylmethylene)amino]phenyl}cyclohexyl)propanoate (2.3 g, 5.23 mmol) in ethanol (50 mL) and the reaction mixture was stirred under a hydrogen atmosphere for 6 h. The reaction mixture was filtered and concentrated in vacuo to leave an oil. The oil was purified by chromatography, using 20-50% EtOAc in isohexane as eluent, to give the title compound (1.0 g, 71%) as an oil; 1H NMR δ (CDCl3) 0.9-1.1 (2H, m), 0.95 (3H, d), 1.1 (3H, t), 1.18-1.32 (2H, m), 1.38-1.5 (1H, m), 1.54-1.64 (1H, m), 1.65-1.8 (3H, m), 2.04-2.15 (1H, m), 2.18-2.3 (1H, m), 3.98 (2H, q), 6.8 (2H, d), 6.92 (2H, d); MS m/e MH+ 276.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customto leave an oil
  4. customThe oil was purified by chromatography

Sources & evidence

ORD record
ord-70247b89f1ed4f41ad8e56de83c06821
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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