Sodium Hydroxide → tert-Butyl 2-Cyclopentylhydrazinecarboxylate

Participants

Reaction Steps

Sodium cyanoborohydride (6.4 g, 0.101 mol) was added portion-wise to a suspension of 1-cyclopentylidenehydrazine-2-carboxylic acid tert-butyl ester (20 g, 0.101 mol) in a mixture of acetic acid and methanol (288 mL, 1:1). The resulting solution was stirred at RT for 2 h. The reaction mixture was neutralized with 1 N aq NaOH and extracted with CH2Cl2. The organic layer was washed with saturated NaHCO3, dried (Na2SO4) and concentrated under reduced pressure to give 1-cyclopentylhydrazine-2-carboxylic acid tert-butyl ester (18.4 g) as an oil.

Provenance & Evidence