HCID 57918267, compound → HCID 59598521, compound

Participants

Reaction Steps

A 50 mL three-necked flask was charged with (R)-tert-butyl 3-(2-tert-butylbenzofuran-7-carbonyl)piperidine-1-carboxylate (0.41 g, 1.08 mmol) and anhydrous THF (8 mL). The flask was evacuated and refilled with N2. The mixture was cooled with dry ice-acetone bath and the Grignard reagent derived from 1-chloro-4-methoxy-butane (5.4 mL, 2M) was added. The reaction mixture was allowed to slowly warm to rt while stirring overnight. The mixture was quenched with satd aq NH4Cl (20 mL) and extracted with EtOAc (3×20 mL). The combined organic extracts were dried over Na2SO4 and concentrated in vacuo to afford (R)tert-butyl 3-((S)-1-(2-tert-butylbenzofuran-7-yl)-1-hydroxy-5-methoxypentyl)piperidine-1-carboxylate (0.5 g, 100%). 1H NMR:(CDCl3): 1.34 (s, 9H), 1.46 (s, 9H), 1.51 (m, 9H), 2.02 (m, 1H), 2.18 (m, 1H), 2.50 (m, 2)H, 2.67 (t, 1H), 3.23 (m, 5H), 3.99 (s, 1H), 4.43 (s, 1H), 6.35 (s, 1H), 7.16 (t, 1H), 7.23 (d, 1H), 7.39 (dd, 1H),

Provenance & Evidence