p-Toluenesulphonyl cyanide → HCID 57332418, compound

Participants

Reaction Steps

(S)-2-(azidomethyl)-1-Boc-pyrrolidine (480 mg, 2.1 mmol) was added to a flask containing p-toluenesulfonyl cyanide (420 mg, 2.3 mmol) and a stir bar (no solvent). The flask was placed in a 80° C. bath and reaction proceeded for 48 hours. The reaction was concentrated in vacuo. The crude amber oil was purified by flash silica gel chromatography using a hexane/ethyl acetate gradient. The product (780 mg, 91% yield) was obtained as a colorless oil. 1H-NMR (500 MHz, CDCl3): δ 8.01 (broad d, J=18 Hz, 2H), 7.44 (m, 3H), 4.85-4.70 (m, 2H), 4.52-4.48 (m, 1H), 3.50-3.34 (m, 2H), 2.49 (s, 3H), 2.01-1.71 (m, 4H), 1.40 & 1.33 (2 s, 9H). ESI-MS (m/z) for C18H25N5O4S (exact mass 407.16): [M+H]+ calc. 408.2, obs. 408.2; [M+Na]+ calc. 430.2, obs. 430.2.

Provenance & Evidence