Lithium borohydride → HCID 60067061, compound

Participants

Reaction Steps

To (2S,4R)-4-Trimethylsilanyloxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester 1.50 g (4.22 mmol) in 5 mL of anhydrous THF under an atmosphere of Ar in an ice bath, was added 2.56 mL LiBH4 (2.0 M in THF, 5.12 mmol) drop-wise. The solution was stirred for 3 h. The mixture was quenched with 1 mL of Sat. NaHCO3 and EtOAc (50 mL). The organics were washed with Sat. NaHCO3 (2×50 mL). The organic layer was dried over Na2SO4 and the solution was concentrated to afford 1.31 g (96%) of (2S,4R)-2-Hydroxymethyl-4-trimethylsilanyloxy-pyrrolidine-1-carboxylic acid benzyl ester as clear oil. HPLC: Rt 2.87 min. (100% area). 1H NMR (CDCl3, 400 MHz) δ 7.26-7.20 (5H, m), 5.05 (2H, s), 4.47 (1H, d, J=7.4 Hz), 4.20 (1H, bs), 4.08 (1H, q, J=7.3 Hz), 3.64 (1H, t, J=9.1 Hz), 3.51-3.47 (1H, m), 3.41-3.35 (2H, m), 1.89-1.84 (1H, m), 1.57-1.52 (1H, m), 0.11 (9H, s). LCMS (ESI) (M+H+) m/z: 324.2.

Provenance & Evidence