Aluminium lithium hydride → HCID 131733442, compound

Participants

Reaction Steps

(R)-tert-Butyl 4-((3-(3-((tert-butoxycarbonyl)amino)-1-hydroxypropyl)phenoxy)methyl)piperidine-1-carboxylate (0.70 g, 1.50 mmol) was added at 0° C. to a suspension of LiAlH4 (0.171 g, 4.5 mmol) in anhydrous THF (10 mL) and the reaction mixture was stirred at room temperature for 1 h. After completion of the reaction as judged by TLC, the reaction mixture was quenched with EtOAc (10 mL) and 10% aqueous NaOH, filtered through Celite, dried over anhydrous Na2SO4 and concentrated under reduced pressure. Purification by column chromatography (CH2Cl2-10% MeOH:CH2Cl2, 0-5% gradient) gave (R)-tert-butyl (3-hydroxy-3-(3-((1-methylpiperidin-4-yl)methoxy)phenyl)propyl)carbamate as a pale yellow semi-solid. Yield (0.50 g, 87%); 1H NMR (400 MHz, CDCl3): δ 7.22 (t, J=4.40 Hz, 1H), 6.92 (s, 2H), 6.76 (d, J=8.0 Hz, 1H), 4.31 (s, 1H), 3.85 (d, J=5.6 Hz, 2H), 3.69 (s, 1H), 3.27 (d, J=6.8 Hz, 2H), 2.58 (s, 2H), 2.46 (s, 2H), 2.04-1.91 (m, 4H), 1.84 (t, J=5.20 Hz, 4H), 1.70-1.67 (m, 1H), 1.45 (s, 9H); MS: m/z 379.28 [M+H]+.

Provenance & Evidence