Diisobutylaluminum hydride → tert-Butyl (3-oxo-2-phenylpropyl)carbamate

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 3-[(tert-butoxycarbonyl)amino]-2-phenylpropanoate from Step A (2.1 g, 7.52 mmol) in anhydrous dichloromethane (75 mL) was cooled to −78° C. under nitrogen and DIBAL-H (15 mL, 15 mmol, 1.0 M in hexanes) was added to the solution dropwise over 45 minutes. This solution was then stirred at −78° C. for 1 h. The reaction was then quenched by the addition of a saturated aqueous solution of Rochel's salt (75 mL) and the biphasic solution was stirred at ambient temperature for 30 minutes. The layers were separated and the aqueous layer was extracted twice with DCM. The combined organics were dried over sodium sulfate, filtered, and concentrated in vacuo to provide a residue. The residue was applied to a silica gel column for purification, eluting with a gradient of 1-3% methanol in DCM to yield the title compound. MS: m/z=250 (M+1).

Provenance & Evidence