Methanol → 4-Azido-5-methyl-1-(pyridine-2-sulfonyl)-azepan-3-ol

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Reaction Steps

5-methyl-3-(pyridine-2-sulfonyl)-8-oxa-3-aza-bicyclo[5.1.0]octane (230 mg, 0.86 mmol) was dissolved in the mixture of 8 ml MeOH and 2 ml H2O. NaN3 (170 mg, 2.6 mmol) and NH4Cl (140 mg, 2.6 mmol) were added to the solution. The resulting mixture was refluxed overnight. After the removal of MeOH, the residue was diluted in EtOAc and washed with 10% NaHCO3 and brine. Purified on column chromatography gave the title compound (170 mg, yield 64%). MS (M+H+) 312.2; 1H-NMR (400 Hz, CDCl3): d=8.69(d, 1H), 8.04-7.94(m, 2H), 7.54 (m, 1H) 4.00-2.95 (m, 7H), 2.20(m, 1H), 1.90-1.74(m, 2H), 0.98(d, 3H)

Provenance & Evidence