HCID 59464121, compound → HCID 178471531, compound

HRID 1713896Notes

Reaction equation

HRID 1713896 reaction equation
C(OC([NH:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]2[CH2:23][CH2:22][C:21](=[C:24]([CH3:30])[C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:20][CH2:19]2)=[CH:14][C:13]=1[Cl:31])=O)C1C=CC=CC=1>C(OCC)(=O)C.[Pt]=O>[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([C@H:18]2[CH2:19][CH2:20][C@H:21]([CH:24]([CH3:30])[C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:22][CH2:23]2)=[CH:14][C:13]=1[Cl:31]

Participants

4

Reactant 1

HCID 59464121HCID 59464121, compound

Product 1

HCID 178471531HCID 178471531, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

Platinum oxide (300 mg) was added in one portion to a stirred solution of ethyl 2-[4-(4-{[(benzyloxy)carbonyl]amino}-3-chlorophenyl)cyclohexylidene]propanoate (1.7 g, 3.85 mmol) in ethyl acetate (50 mL) and the mixture was stirred at room temperature under a hydrogen atmosphere for 9 h. The reaction mixture was filtered and concentrated in vacuo to leave a residue, which was purified by column chromatography, using a gradient of 11-66% ethyl acetate:isohexane as eluent, to give the aniline product as a mixture of cis- and trans-cyclohexane isomers. Recrystallisation from a mixture of ethanol and diethyl ether gave the title compound (0.37 g, 28%) as a white solid; 1H NMR δ 1.08 (3H, d), 1.2-1.3 (1H, m), 1.27 (3H, t), 1.31-1.49 (1H, m), 1.52-1.7 (1H, m), 1.71-1.81 (1H, m), 1.81-1.97 (3H, m), 2.2-2.32 (1H, m), 2.33-2.48 (1H, m), 4.15 (2H, dq), 7.02 (1H, dd), 7.2 (1H, d), 7.22 (1H, d); MS m/e MH+ 310.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customto leave a residue, which
  4. customwas purified by column chromatography

Sources & evidence

ORD record
ord-4bbfe807df634212afd6bda7010217cd
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

Loading…