N-bromobutanimide → tert-Butyl 4-(2-Bromoacetyl)piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

Dissolve the title compound from Step A above (6.0 g, 20 mmol) in THF (120 mL), cool to 0° C. and add sodium bicarbonate. To the resulting suspension was added NBS and the mixture stirred for 1.5 h. TLC showed no starting material left. Poured reaction into sat'd aqueous sodium buicarbonate solution (200 mL) and extracted with ether (2×200 mL). The organics were combined, washed with water and brine, dried over magnesium sulfate, filtered and concentrated under vacuum. The resulting product (6.4 g, 99%) was used without further purification for the next reaction. ESI-MS calculated for C12H20BrNO3: Exact Mass: 305.06. Found: 305.15 (M)+ and 307.09 (M+2)+.

Provenance & Evidence