Diisopropylamine → HCID 22496050, compound

Participants

Reaction Steps

LDA was prepared by addition of n-BuLi (2.5 M in hexanes, 1.93 mL, 4.83 mmole) to a solution of diisopropylamine (0.63 mL, 4.83 mmole) in dry THF (5 mL) at 0° C. The LDA solution was added dropwise to a solution of 2-(tert-butyldimethylsilyloxy)-2-(pyridin-3-yl)acetonitrile (1.0 g, 4.03 mmole) in dry THF (15 mL) at −78° C. The solution was stirred for 15 min, then 1 benzyloxybenzyl chloride (1.41 g, 6.05 mmole) was added as a solid all at once. The reaction was kept at −78° C. for 15 min, then was warmed to RT. After 30 min at RT, the reaction was quenched with saturated aqueous NH4Cl and stirred for 20 min. EtOAc extraction (3×), drying (MgSO4), concentration, and flash chromatography on silica gel (20% EtOAc/hexanes) gave the title compound (769 mg, 43%) as a yellow oil: 1H NMR (300 MHz, CDCl3) δ 8.80 (narrow m, 1 H), 8.67-8.70 (m, 1 H), 7.75-7.80 (m, 1 H), 7.33-7.53 (m, 6 H), 7.08 (d, 2 H), 6.93 (d, 2 H), 5.10 (s, 2 H), 3.30 (½ Abq, 1 H), 3.18 (½ Abq, 1 H), 0.99 (s, 9 H), 0.12 (s, 3H), 0.08 (s, 3H).

Provenance & Evidence