Hydrochloric Acid → ethyl (3S,4S)-4-t-butoxycarbonylamino-3-hydroxy-6-methylheptanoate

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Reaction Conditions

Reaction Steps

To diisopropylamine (7.7 gm, 0.077 mole) in dry tetrahydrofuran (26 mL) cooled to -20° C. under an argon atmosphere was added dropwise n-butyllithium in hexane (1.46 m, 52.4 mL, 0.077 mole). The solution was stirred 15 minutes, the temperature lowered to -78° C. and dry ethyl acetate (6.7 g. 0.077 mole) added dropwise while maintaining the temperature below -75° C. The solution was stirred 10 minutes and a precooled (-78° C.) tetrahydrofuran solution of Boc-L-leucinal (11 gm., 0.051 mole) was added. After 30 minutes, 2M HCl (40 mL) was added and the mixture was slowly warmed to 10° C. and extracted with ether (3×200 mL). The combined ethereal extract was washed with saturated sodium chloride (NaCl) and dried with magnesium sulfate (MgSO4) and filtered. Evaporation of the filtrate in vacuo gave 14 gm of crude product which was purified by flash column chromatography (20% ethylacetate in hexane). Obtained 6 gm of Boc-Sta-OEt.

Provenance & Evidence