N-(4-Hydroxycyclohexyl)isobutyramide → 2-Methyl-N-(4-oxocyclohexyl)propanamide

Participants

Reaction Steps

Add pyridinium chlorochromate (561.6 g, 2.61 mol) to N-(4-hydroxycyclohexyl)isobutyramide (321.8 g, 1.74 mol) in CH2Cl2 (8000 mL) and stir mechanically for 24 h under nitrogen. Add silica gel (2000 g), stir, and filter through a silica pad (6000 g). Elute with CH2Cl2 followed by 75-100% EtOAc/hexanes to obtain 210 g of a light brown solid (66%/o). MS (ES): m/z 184 (M+1); 1H NMR(DMSO-d6): δ 5.54 (br s, NH), 4.27 (septet, 1H), 2.20-2.60 (m, 7H), 1.78 (m, 2H), 1.15 (d, 6H).

Provenance & Evidence