4-(3-Chloropyridin-2-yl)-4-methylcyclohex-2-enone → 4-(3-Chloropyridin-2-yl)-4-methylcyclohexanone

HRID 661377Notes

Reaction equation

HRID 661377 reaction equation
[Cl:1][C:2]1[C:3]([C:8]2([CH3:15])[CH2:13][CH2:12][C:11](=[O:14])[CH:10]=[CH:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[H][H]>CN(C=O)C.[Pt]>[Cl:1][C:2]1[C:3]([C:8]2([CH3:15])[CH2:9][CH2:10][C:11](=[O:14])[CH2:12][CH2:13]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 674999494-(3-Chloropyridin-2-yl)-4-methylcyclohex-2-enoneHCID 178418361HCID 178418361, compound

Product 1

HCID 674987224-(3-Chloropyridin-2-yl)-4-methylcyclohexanoneYield 40%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of the product of Example 38E (0.225 g, 1.015 mmol) in DMF was added to 5% Pt—C, wet (225 mg, 1.153 mmol) in a 50 ml pressure bottle. The mixture was pressurized with hydrogen (40 psi), stirred for 16 hours at ambient temperature, filtered to remove catalyst, and concentrated. The residue was chromatographed on silica gel eluting with 30% ethyl acetate-hexanes to give the title compound (90 mg, 40%). 1H NMR (300 MHz, DMSO-d6) δ ppm 8.55 (dd, J=1.5, 4.6, 1H), 7.91 (dd, J=1.5, 8.0, 1H), 7.36 (dd, J=4.6, 8.0, 1H), 2.96-2.77 (m, 2H), 2.26 (dd, J=5.4, 8.1, 4H), 2.03-1.84 (m, 2H), 1.46 (s, 3H). MS (DCI) m/z 224 (M+H)+.

Workup

  1. filtrationfiltered
  2. customto remove catalyst
  3. concentrationconcentrated
  4. customThe residue was chromatographed on silica gel eluting with 30% ethyl acetate-hexanes

Sources & evidence

ORD record
ord-eea5fdaee85d4ff9ba9086fc684d83cc
Source dataset
uspto-grants-2011_12
Patent number
US08084616B2

Reaction notes

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