Hydride → HCID 86588220, compound

Participants

Reaction Steps

To (S)-N-methoxy-N-methyl-3-[2-(2-naphthalen-1-yl-ethoxy)-4-pyrrolidin-1-yl-benzenesulfonylamino]-succinamic acid tert-butyl ester (1.0 g, 1.60 mmol) solution in dry THF/Et2O (2:1, 30 mL) at −65° C. was added LiAlH4 (6.50 mL, 6.5 mmol, 1.0 M solution in Et2O). The reaction mixture temperature was maintained for 2 h. The excess hydride was quenched by the addition of potassium hydrogen sulfate (2 equiv) dissolved in water. After warming to room temperature, Et2O was added (100 mL) and the organic layer was washed with water and then with brine. The solvent was dried (MgSO4), filtered, and evaporated to dryness. The resulting crude product was purified on silica gel flash chromatography (25% EtOAc in hexanes) to give (S)-3-[2-(2-naphthalen-1-yl-ethoxy)-4-pyrrolidin-1-yl-benzenesulfonyl amino]-4-oxo-butyric acid tert-butyl ester as a off white foam (0.60 g, 68%). MS (APCI) m/z 551.3 (M−1).

Provenance & Evidence