Triethylamine → (3S,4S)-N-Cbz-3-azido-4-hydroxypyrrolidine

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Reaction Conditions

Reaction Steps

A sample of the (3S,4S)—N-Boc-3-azido-4-hydroxypyrrolidine (80 mg, 0.35 mmol) was dissolved in trifluoroacetic acid (1 mL) and was stirred until no starting material was detected on TLC (25% ethyl acetate in hexane). The solution was evaporated under reduce pressure and the residue was dissolved in CH2Cl2 (2 mL). The solution was cooled to 0° C., triethylamine (117 μL, 0.84 mmol) and Cbz-Cl (60 mg, 0.35 mmol) were added, and the resulting solution was stirred for 2 hr at room temperature. The reaction mixture was washed with water, dried over Na2SO4, and evaporated. The residue was purified by flash chromatography (25% ethyl acetate in hexane) to give (3S,4S)—N-Cbz-3-azido-4-hydroxypyrrolidine (89 mg, 97%): [α]20D=+ 16.1° (c=1.00, CHCl3). Lit. [Kamal, A.; Shaik, A. A.; Sandbhor, M.; Malik, M. S.; Kaga, H. Tetrahedron Lett. 2004, 45, 8057-8059] for (3S,4S)—N-Cbz-3-azido-4-hydroxypyrrolidine: [0]25D=+14.3° (c=1.06, CHCl3).

Provenance & Evidence