Trimethylsilyl iodide → (S)-3-Amino-N-cyclopropyl-N-(2,3-dichlorobenzyl)-4-hydroxybutanamide

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Reaction Steps

Into a 1L round bottom flask fitted with a nitrogen inlet was added 4A (18.3 g, 40.6 mmol) and acetonitrile (450 mL). Trimethylsilyliodide (TMSI) (17.4 mL, 121.7 mmol, 3 eq) was added quickly at room temperature. After stirring for 15 minutes, the reaction was quenched with 50 mL of methanol. The solvent was removed under vacuum. The residue was partitioned between ethyl acetate (100 mL) and saturated sodium bicarbonate (50 mL). The organic layer was separated and the aqueous layer was extracted further with ethyl acetate (2×50 mL). The organic layers were combined and washed once with brine (50 mL). The organic phase was dried over sodium sulfate and filtered. Solvent was removed under vacuum and the residue was purified by column chromatography (5% methanol/1% triethylamine/DCM) to give 10.6 g of 4B (69%). ESI-MS:m/z 317.3 (M+H)+.

Provenance & Evidence