Aluminium lithium hydride → HCID 66889504, compound

Participants

Reaction Steps

1,1-Dimethylethyl 4-[({2-(methyloxy)-5-[(methyloxy)carbonyl]phenyl}oxy) methyl]piperidine-1-carboxylate (3.34 g, 8.8 mmol) was dissolved in THF (30 mL) and the resulting solution was cooled with an ice bath. A solution of LAH in THF (1 M, 8.8 mmol, 8.8 mL) was added by syringe. The reaction vessel was removed from the ice bath, and the reaction mixture was allowed to warm to rt. After 2 h at rt, the mixture was quenched by cautious sequential addition of water (0.33 mL), 15% NaOH (aq) (0.33 mL), and water (1 mL). During the quench, a white precipitate formed. The solid was removed by filtration through celite and was rinsed with ether. The combined organic layers were washed with dilute hydrochloric acid to then dried over sodium sulfate, filtered, and concentrated to provide 1.88 g of 1,1-dimethylethyl 4-({[5-(hydroxymethyl)-2-(methyloxy)phenyl]oxy}methyl)piperidine-1-carboxylate (5.4 mmol, 61% yield). 1H NMR (400 MHz, CDCl3): δ6.93-6.85 (m, 3H), 4.62 (d, 2H), 4.15 (br m, 2H), 3.87 (m, 2H), 3.86 (s, 3H), 2.76 (br m, 2H), 2.06 (m, 1H), 1.88 (br d, 2H), 1.47 (s, 9H), 1.28 (m, 2H).

Provenance & Evidence