Benzyl Bromide → HCID 69428146, compound

Participants

Reaction Steps

To a stirred solution of compound 1D (0.403 g, 1.17 mmol) in 5 mL of THF at room temperature under argon was added (in one portion) 1.20 mL (in THF, 1.2 mmol) of 1M lithium bis(trimethylsilyl)amide and, after 5 min, 153 μL of benzyl bromide (1.29 mmol). After 15 h, additional portions of the base and alkylating agent were added as before. After 1 h more, the reaction mixture was quenched with saturated NaCl and extracted twice with EtOAc. The combined organic extracts were dried over MgSO4, filtered and evaporated under reduced pressure. Purification by silica gel chromatography (7:33 EtOAc/CH2Cl2) provided the title compound (394 mg, 77%) as a colorless oil and a 61:39 mixture of diastereomers of unknown assignment. MS [M+H]+: found 435.

Provenance & Evidence