Triphenylphosphine → Benzyl 3-acetylsulfanylazetidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To triphenylphosphine (4.40 g, 16.8 mmol) in tetrahydrofuran (25 mL, THF) at -78 ° C. was added diethylazodicarboxylate (2.60 mL, 16.5 mmol) in THF (15 mL). After 7 min thiolacetic acid (1.25 mL, 17.5 mmol) in THF (15 mL) was added followed by, after 7 min, the resultant compound from Example 112 (2.789 g, 13.46 mmol). The mixture was stirred at -78 ° C. for 1 h and at room temperature for 20 h, and was then evaporated and chromatographed on silica gel with 20% ethyl acetate in hexane affording 3.250 g (91%) of a white solid, m.p. 94.5°-95.5 ° C. TLC (20% ethyl acetate/80% hexane) Rf =0.17; 1H NMR (CDCl3) 7.28-7.41 (m, 5H), 5.09 (s, 2H), 4.48 (d, 1H), 4.44 (d, 1H), 4.15-4.26 (m, 1H), 3.92 (d, 1H), 3.89 (d, 1H) 2.34 (s, 3H).

Provenance & Evidence