Carbon Dioxide → Benzyl 11-(methoxy(methyl)amino)-11-oxoundecylcarbamate

Participants

Reaction Conditions

Reaction Steps

A solution of 19 (2.25 g, 6.44 mmol), methyl methoxyamine hydrochloride (1.26 g, 12.88 mmol) and THF (anhydrous, 30 mL) was cooled to −15 to −20° C. with an ice/methanol bath containing a few pieces of dry ice. To this cold solution was added dropwise i-PrMgCl (3M solution in pentane, 11.27 mL, 22.54 mmol) over 15 min and temperature was then raised to −10° C. and stirring continued at the temperature for additional 2 h. After this time the reaction was quenched by the slow addition of saturated aqueous NH4Cl (50 mL). The aqueous layer was separated and washed with dichloromethane (2×50 mL). Organics were combined, dried over anhydrous Na2SO4, concentrated and further dried under high vacuum overnight to afford the desired product 20 (2.04 g, 84% yield) as a colorless, viscous oil: 1H NMR (300 MHz, CDCl3) δ 1.27 (m, 12H), 1.48 (m, 2H), 1.60 (m, 2H), 2.40 (m, 2H), 3.18 (m, 5H), 3.68 (s, 3H), 5.09 (s, 2H), 7.34 (m, 5H); m/z (ESI) 379 [M+H]+.

Provenance & Evidence