Methyl morpholine oxide → HCID 11645212, compound

Participants

Reaction Conditions

Reaction Steps

Charge a flask with 3-(2-bromo-6-chloro-benzyl)-1-cyclohexyl-pyrrolidin-2-one (Example 56) (210 mg, 0.57 mmol), bis(neopentyl glycolato)diboron (150 mg, 0.68 mmol), KOAc (200 mg, 2.0 mmol) and Pd(dppf)Cl2 (23 mg, 0.03 mmol) and purge with nitrogen. Add DMSO (5 mL) and plunge into an 80° C. oil bath and stir under nitrogen for 24 hours. Cool to room temperature and pour into water. Extract with ether. Dry over sodium sulfate, filter and concentrate. Dissolve residue in 1N NaOH (10 mL) and stir at room temperature overnight. Extract water with ether and acidify the aqueous layer with HCl. Extract with ether, dry over sodium sulfate, filter and concentrate. Dissolve residue in THF (5 mL) and add N-methyl morpholine N-oxide (200 mg, 1.7 mmol) and heat to reflux for 6 hours. Cool to room temperature and pour into saturated aqueous sodium bisulfite. Extract with methylene chloride. Dry over sodium sulfate, filter and concentrate. Purify over silica gel (3:1 to 1:1 hexanes:ethyl acetate). Triturate the recovered material with 2:1 hexanes:ethyl acetate to afford 47 mg (27%) of the title compound as a white solid. Mass spectrum (apci) m/z=308.1 (M+H).

Provenance & Evidence