HCID 67158968, compound → HCID 67159110, compound

HRID 1892002Notes

Reaction equation

HRID 1892002 reaction equation
[Si:1]([O:18][CH2:19][CH:20]1[CH2:25][CH2:24][CH:23]([OH:26])[C:22]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([C:35]([F:38])([F:37])[F:36])[CH:29]=2)([CH3:27])[CH2:21]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl.CCOCC>[Si:1]([O:18][CH2:19][CH:20]1[CH2:25][CH2:24][C:23](=[O:26])[C:22]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([C:35]([F:38])([F:36])[F:37])[CH:29]=2)([CH3:27])[CH2:21]1)([C:14]([CH3:15])([CH3:16])[CH3:17])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 67158968HCID 67158968, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 67159110HCID 67159110, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of (1RS,2RS,4RS)-4-((tert-butyldiphenylsilyloxy)methyl)-2-(4-chloro-3-(trifluoromethyl)phenyl)-2-methylcyclohexanol (1.35 g, 2.406 mmol) in dichloromethane (40 mL) was treated with Celite (1.5 g, 24.97 mmol) and pyridinium chlorochromate (0.778 g, 3.61 mmol). The resulting mixture was stirred at rt for 19.5 h, then diluted with Et2O and stirred vigorously at rt. The resulting slurry was filtered through a pad of Florisil and the solids were rinsed thoroughly with Et2O. The filtrate was concentrated under vacuum, taken up in dichloromethane and concentrated. The resulting residue was purified by column chromatography on silica gel, eluting with 0-15% ethyl acetate-hexane, to provide (2RS,4RS)-4-((tert-butyldiphenylsilyloxy)methyl)-2-(4-chloro-3-(trifluoro-methyl)phenyl)-2-methylcyclohexanone as a colorless gum (1.338 g, 99%). 1H NMR (400 MHz, CDCl3) δ 7.66 (m, 4 H), 7.53 (d, J=2.0 Hz, 1 H), 7.43 (m, 7 H), 7.26 (m, 1 H), 3.58 (dd, J=9.8, 5.5 Hz, 1 H), 3.48 (dd, J=9.8, 7.1 Hz, 3 H), 2.79 (dt, J=14.6, 3.0 Hz, 1 H), 2.33 (m, 2 H), 2.07 (m, 1 H), 1.93 (m, 1 H), 1.49 (dd, J=14.6, 12.6 Hz, 1 H), 1.41 (m, J=12.5, 4.9 Hz, 1 H), 1.26 (s, 3 H), 1.09 (s, 9 H).

Workup

  1. stirringstirred vigorously at rt
  2. filtrationThe resulting slurry was filtered through a pad of Florisil
  3. washthe solids were rinsed thoroughly with Et2O
  4. concentrationThe filtrate was concentrated under vacuum
  5. concentrationconcentrated
  6. customThe resulting residue was purified by column chromatography on silica gel
  7. washeluting with 0-15% ethyl acetate-hexane

Sources & evidence

ORD record
ord-3243e9584cd84d40bd86e7280d9eac36
Source dataset
uspto-grants-2013_08
Patent number
US08507559B2

Reaction notes

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