Chlorotrimethylsilane → HCID 59702321, compound

Participants

Reaction Steps

A mixture of sodium cyanoborohydride (0.276 g, 4.39 mmol), 5 mL of THF, and TMSCl (0.56 mL, 4.4 mmol) was stirred for 10 m, then 45 (0.780 g, 3.67 mmol) in 10 mL of THF was slowly added. The mixture was stirred for 1 h, then 15 mL of a 2 M aqueous NaOH solution were added. The mixture was extracted with 40 mL of diethyl ether, and the organic layer was washed with two 20 mL portions of a saturated aqueous NaCl solution, dried over Na2SO4, filtered, and concentrated. Column chromatography (0→20% EtOAc/hexanes) afforded N′-cyclopropylmethyl-N-ethyl-hydrazinecarboxylic acid tert-butyl ester (46; 0.323 g; 41%).

Provenance & Evidence