Sodium Azide → (2S,4R)-tert-butyl 2-(azidomethyl)-4-hydroxypyrrolidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of the product from Example 174A (365 mg, 1.021 mmol) in N,N-dimethylformamide (5 mL) was added sodium azide (531 mg, 8.17 mmol), and the reaction mixture was stirred at 55° C. for 8 hours. The resulting mixture was purified by flash chromatography on a 12 g silica gel column, eluting with 5% ethyl acetate//hexanes for 3 minutes followed by a gradient to 100% ethyl acetate over 20 minutes to afford the title compound as an oil (135 mg, 54.6%). 1H NMR (400 MHz, DMSO-d6) δ ppm 4.65 (d, J=3.5 Hz, 1H), 4.24 (d, J=3.5 Hz, 1H), 3.97 (ddd, J=10.2, 7.6, 3.1 Hz, 1H), 3.64 (dd, J=12.3, 5.5 Hz, 1H), 3.39-3.22 (m, 3H), 2.01-1.80 (m, 2H), 1.42 (s, 9H); MS (DCI) m/z 243 (M+H)+.

Provenance & Evidence