Hydrochloric Acid → HCID 86680655, compound

Participants

Reaction Steps

To a solution of tert-butyl (3R)-3-(4-methoxycarbonylphenyl)morpholine-4-carboxylate 9 (6.91 g, 21.50 mmol) in THF (140 mL) was added lithium borohydride (1.873 g, 86.00 mmol) and the resulting mixture then heated under reflux overnight. Additional lithium borohydride (341 mg, 2 eq) was added and the reaction mixture heated under reflux for 2 h. The reaction mixture was cooled in an ice bath and then added ice-water, followed by 2M HCl (10 mL) and stirred until effervescence ceased then diluted with EtOAc (100 mL), mixed and the organic layer separated, washed sequentially with water (1×50 mL), brine (1×50 mL), dried over MgSO4, filtered and concentrated in vacuo to leave the product as a colourless viscous oil (6.0 g, 95% yield); 1H NMR (400.0 MHz, DMSO) d 1.40 (9H, s), 3.01 (1H, m), 3.49 (1H, m), 3.71-3.83 (3H, m), 4.27 (1H, m), 4.47 (2H, m), 4.96 (1H, s), 5.17 (1H, m) and 7.30 (4H, m) ppm.

Provenance & Evidence