Benzylamine → HCID 66773807, compound

Participants

Reaction Conditions

Reaction Steps

In a pressure tube was placed a solution of crude [(1S,2R,3R,4S)-4-hydroxy-3-(2-methylphenyl)cyclohexane-1,2-diyl]di(methylene) dipropanesulfonate (Step 1.85 g, 184 mmol) in ˜120 mL ethanol and benzylamine (70.2 mL, 643 mmol). The pressure tube was sealed and heated at 140° C. in an oil bath for 3 hr. The tube was cooled to RT and opened. LC-MS showed that the reaction was completed. The resulting mixture was diluted with 180 mL methanol and 100 mL 5 N aq. NaOH. The ethanol, some of water and benzylamine were removed under vacuum. The residue was dissolved in ethyl acetate and diluted with water. The organic layer was separated and the aqueous was extracted with ethyl acetate. The combined organic layers were dried over MgSO4, filtered and the solvent was evaporated under vacuum. The combined organics were concentrated, and the residue oil was purified by column chromatography (1:9 methanol:ethyl acetate. 1H-NMR (CDCl3): δ: 7.35-7.10 (9H, m), 3.81-3.62 (3H, m), 2.94 (1H, t, J=8.1 Hz), 2.83 (1H, t, J=10.0 Hz), 2.52 (2H, m), 2.40 (1H, t, J=10.0 Hz), 2.36 (3H, s), 2.20 (1H, m), 2.02-1.85 (3H, m), 1.60 (1H, m), 1.36 (1H, m). M++1: 322.19.

Provenance & Evidence