Hexamethylphosphoramide → (3S,5S,6R)-3-(5-Chloro-pentyl)-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid tert-butyl ester

참여 물질

반응 조건

반응 단계

A 1.0M solution of sodium bis(trimethylsilyl)amide in THF (55.0 mL, 55.2 mmol) is added at −78° C. to a solution of (5S,6R)-5,6-diphenyl-4-tert-butoxycarbonyl-morpholin-2-one (13.0 g, 36.8 mmol), 1-chloro-5-iodo-pentane (25.0 g, 108.0 mmol) and HMPA (55.0 mL) in THF (200.0 mL). The reaction mixture is stirred at −78° C. for 2 hours and at room temperature for 1 hour. The reaction mixture is diluted with EtOAc, washed with water and brine. After drying the organic phase over anhydrous Na2SO4, the solvent is removed under reduced pressure to afford the crude product that is purified by silica gel column chromatography to afford the title compound; m/z 358 [M-Boc+H].

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