Ammonium Hydroxide → HCID 18650089, compound

Participants

Reaction Steps

To a solution of 50 mg of methyl (2R-cis)-3-(benzyloxymethyl)oxirane carboxylate in 3 ml of MeOH was added 1 ml of concentrated NH4OH with rapid stirring. The mixture was allowed to stir for two days. The reaction was then diluted with 20 ml of CHCl3 and the organic layer separated and washed three times with 10 ml of 0.1N HCl. The combined organic layers were dried over MgSO4, filtered and evaporated to yield a pale yellow residue. Flash chromatography (7 mm column, 5% MeOH: CHCl3) afforded 24.2 mg of a clear oil which solidified upon standing. 1H NMR (CDCl3) 7.4-7.2 (m, 5), 6.08 (br, 1), 5.64 (br, 1), 4.58 (dd, 2, J=12, 15 Hz), 3.8 (m, 1), 3.5-3.4 (m, 3). Mass Spectra: EI: M-41 (--CONH2) Calc. 163.0758, Found 163.0745.

Provenance & Evidence