Allyl iodide → 3-((2R,5R)-2-Allyl-5-cyclohexyl-3-oxo-morpholin-4-yl)-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-((R)-3-Cyclohexyl-5-oxo-morpholin-4-yl)-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid methyl ester (600 mg, 1.49 mmol, 1.0 equiv) in THF (5.0 mL) at −78° C. was added LDA (0.82 mL, 2.0 M in THF, 1.64 mmol, 1.1 equiv) and the resulting solution was stirred at −78° C. for 20 minutes. To the solution was then added allyliodide (300 mg, 1.78 mmol, 1.2 equiv). The solution was warmed to room temperature and stirred at this temperature for 30 minutes. The reaction was quenched by addition of sat. aq. NH4Cl solution. The mixture was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel column chromatography, EtOAc/heptane 25% to give 3-((2S,5R)-2-Allyl-5-cyclohexyl-3-oxo-morpholin-4-yl)-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid methyl 140 mg, 3-((2R,5R)-2-Allyl-5-cyclohexyl-3-oxo-morpholin-4-yl)-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid methyl ester 60 mg and mixed fraction 200 mg.

Provenance & Evidence