[1(S)-(Methoxy-methyl-carbamoyl)-2,2-dimethylpropyl]-carbamic Acid-tert-butyl Ester → (1(S)-Acetyl-2,2-dimethylpropyl)carbamic Acid-tert-butyl Ester

Participants

Reaction Conditions

Reaction Steps

[1(S)-(Methoxy-methyl-carbamoyl)-2,2-dimethylpropyl]-carbamic acid-tert-butyl ester (2.0 g, 7.3 mmol) was dissolved in, freshly distilled THF under an argon atmosphere. The solution was cooled to −78° C. whereupon MeLi (15.6 mL, 1.4 M in diethyl ether, 21.9 mmol, 3 eqv) was added dropwise maintaining an internal temperature <−70° C. The reaction was stirred at −70° C. for 30 minutes before warming to −30° C. for a further 30 minutes. After this time TLC analysis indicated the complete consumption of starting material. Saturated aqueous ammonium chloride solution (10 mL) was added and the reaction allowed to warm to room temperature. The aqueous phase was extracted with ethyl acetate (3×30 mL). The organic phases were washed with water (3×50 mL) and brine (50 mL), dried over MgSO4, filtered and the solvents removed in vacuo to give a crude yellow oil. Purification by column chromatography (SiO2, 20% ethyl acetate in hexanes) afforded the title compound as a colourless oil (1.355 g, 84%).

Provenance & Evidence