1,2-Diaminocyclohexane, trans- → HCID 59991040, compound

Participants

Reaction Steps

A mixture of (1R,2R)-cyclohexane diamine (20 g, 175 mmol) and sodium triacetoxyborohydride (25 g, 120 mmol) in dichloromethane (550 mL) was added with a solution of tert-butyl 4-oxopiperidine-1-carboxylate (18.4 g, 92 mmol) in dichloromethane (800 mL) dropwise over a period of 45 minutes and stirred at room temperature overnight. An aqueous solution of sodium bicarbonate (5%, 200 mL) was added to the reaction mixture, layers were separated, and the aqueous layer was extracted with dichloromethane (2×150 mL). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo to afford the crude product which was purified by dry column vacuum chromatography to give the title compound as a pale yellow oil (18.0 g, 66%). 1H NMR (300 MHz, METHANOL-D4): δ ppm 3.99 (td, J=13.3, 3.3 Hz, 2H), 2.95-2.70 (m, 3H), 2.40-2.15 (m, 2H), 2.05 (m, 1H), 1.95-1.85 (m, 2H), 1.85-1.65 (m, 3H), 1.44 (s, 9H), 1.95-1.35 (m, 6H)

Provenance & Evidence