Benzyl Bromide → HCID 70049710, compound

Participants

Reaction Steps

Lithium diisopropylamide was prepared by the addition of 2.5M N-butyl lithium (610 μL, 1.53 mmol) in hexanes to a solution of diisopropylamine (200 μL, 1.53 mmol) in tetrahydrofuran (3 mL) at 0° C. and stirring for 20 minutes. Then a solution of 4-[4-(4-chlorophenoxy)phenylsulfonylmethyl]-tetrahydropyran-4-carboxylic acid methyl ester (540 mg, 1.27 mmol) in tetrahydrofuran (1 mL) was added to the solution of lithium diisopropylamide at -78° C., and stirred for an additional 60 minutes. Benzyl bromide (181 μL, 1.53 mmol) of was added to the mixture, stirred for an 50 minutes, warmed to room temperature over 30 minutes, and stirred for an additional 3 hours. The mixture was then diluted with 0.1M aqueous hydrochloric acid (25 mL) and extracted with methylene chloride (2×50 mL). The combined organic layers were dried over magnesium sulfate, concentrated in vacuo, chromatographed over silica gel, eluted with 20% ethyl acetate/hexanes, to afford 3-benzyl-4-[4-(4-chlorophenoxy)phenylsulfonylmethyl]-tetrahydropyran-4-carboxylic acid methyl ester (440 mg, 67%) . IR (KBr) 1736 cm-1 ; 1HNMR (CDCl3) δ 1.78 (dm, J=13.5 Hz, 1H), 2.02-2.17 (m, 2H), 2.39 (dm, J=13.5 Hz, 1H), 3.19-3.23 (m, 2H), 3.37-3.45 (td, J=11.9, 2.4 Hz, 2H), 3.77-3.85 (m, 1H), 3.84 (s, 3H), 3.88-3.98 (m, 2H), 4.07-4.17 (m, 2H), 6.83-6.90 (m, 4H), 6.94 (d, J=8.7 Hz, 2H), 7.08-7.15 (m, 3H), 7.37 (d, J=8.7 Hz, 2H), 7.62 (d, J=8.7 Hz, 2H); FABMS (M+ +H): 515.

Provenance & Evidence