Tert-butyl 4-(2-iodoethyl)piperidine-1-carboxylate → HCID 131719080, compound

Participants

Reaction Conditions

Reaction Steps

A solution of glycine benzaldehyde imine (10.2 g, 53 mmol) in 100 ml of THF was added dropwise to a cooled (-78° C.) and stirred solution of potassium t-butoxide (5.8 g, 52 mmol) in 300 ml THF over 20 min. After 15 min. a solution of Boc-4-(2-iodoethyl) piperidine (1-6) (18.2 g, 52 mmol) was added and stirring continued at -78° C. for 2 h. followed by standing at -20° C. for 18 h. After stirring 2 h. at r.t., the reaction mixture was concentrated to 50% of volume, poured into ice cold saturated NH4Cl and extracted with ether. The organic phase was washed with brine, dried (MgSO4) and the solvent evaporated. 1 g of the resulting oil was dissolved in 10 ml of methanol, cooled to 0° C. and 100 mg of sodium borohydride added in portions over 5 mins. After an additional 10 min., the reaction was concentrated, poured into water and extracted with ether. The organic extracts were washed with brine, dried (MgSO4) and solvent evaporated to give crude product purified by flash column chromatography (5:1→2:1 hexane:EtOAc) to afford 410 mg of 4-1.

Provenance & Evidence