HCID 20694322, compound → HCID 20694318, compound

Participants

Reaction Steps

To a solution of 5.84 g (13.1 mmol) of (S)-N-[(1-Benzyl)-4-(R)-(3-thienyl)-3-(S)-pyrrolidinylcarbonyl]-4-benzyl-2-oxazolidinone (Step 2) in 60 mL of THF at 0° C. was added 15.7 mL (15.7 mmol) of a solution of LiAlH4 (1.0 M in ether). The solution was stirred at room temperature for 3 h, then was quenched by addition of 5N NaOH solution. The mixture was diluted with ether and the organic fraction was washed twice with 5N NaOH solution. The combined organic fractions were dried over Na2SO4, filtered, and the filtrate concentrated. The residue was purified by chromatography (silica, acetone:hexanes, 1:6) to afford 3.22 g of the title compound. 1H NMR (CDCl3) δ7.33-7.34 (m, 4H), 7.26-7.30 (m, 2H), 7.02-7.04 (m, 2H), 3.77 (d of d, 1H, J=10.3, 4.3 Hz), 3.68 (d of d, 1H, J=10.1, 5.0 Hz); Mass spectrum (ESI) m/e=274 (M+1); [α]D=−13.6 (c.=1.60, CHCl3).

Provenance & Evidence