Sodium Azide → HCID 57029350, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (2S,4R)-1-p-methoxybenzyloxycarbonyl-4-hydroxypyrrolidine-2-methanol p-toluenesulfonate (8.7 g: 20 mmole) in dimethylformamide (60 ml), a solution of sodium azide (1.56 g) in water (6 ml) is added. The mixture is stirred at 80° C. overnight. The reaction mixture is poured into ice water and extracted with ethyl acetate. The extract is successively washed with water and brine, dried over magnesium sulfate, and concentrated in vacuo to give crude (2S,4R)-1-p-methoxybenzyloxycarbonyl-4-hydroxy-2-azidomethylpyrrolidine (5.6 g). Yield: 92%. NMR δ(CDCl3) ppm: 1.95 to 2.1(m, 2H), 3.2 to 3.8(m, 3H), 3.81(s, 3H), 3.83 to 4.6(m, 3H), 5.07(s, 2H), 6.89(d, J=8.8 Hz, 2H), 7.31(d, J=8.8 Hz, 2H). IR ν (CHCl3) cm-1 : 3420, 2100, 1689.

Provenance & Evidence