Diisopropylamine → HCID 58171524, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of diisopropylamine (6.3 g, 62.7 mmol) in dry THF (120 mL) at −20° C. under N2 was added 2.5 M n-BuLi (25.1 mL, 62.7 mmol). The resulting solution was added dropwise to a stirred solution of 1-(2-adamantyl) 3-ethoxycarbonylpiperidine-1-carboxylate (14.0 g, 41.8 mmol) in dry THF (170 mL) at −70° C. The mixture was stirred for 1 h at −70° C. and 2-methoxybenzyl bromide (10.9 g, 54.3 mmol) was added. The mixture was stirred for 4 h at rt, quenched with brine and extracted with CH2Cl2. The organic layer was dried over Na2SO4, concentrated and purified by column chromatography to afford the title compound (14.3 g, 75%). LC-MS Method 3 tR=2.04 min, m/z=456.

Provenance & Evidence