1,1-Dibromoethane → HCID 66850126, compound

Participants

Reaction Conditions

Reaction Steps

cis-2,3-Dihydroxy-piperidine-1-carboxylic acid tert-butyl ester (0.246 g, 1.13 mmol) was dissolved in dibromoethane (1.7 mL) and tetrabutyl ammonium bromide (71 mg, 2.2 mmol) was added. Sodium hydroxide (50% aqueous solution, 17.8 g) was added slowly over 10 minutes at 50° C. A further amount of dibromoethane (7.4 mL, 105.5 mmol in total) was added and the mixture was heated at 55° C. overnight. Dibromoethane (3 mL) was added and the mixture was heated at 55° C. for a further 4 hours and then diluted with water and extracted with DCM (×2). The organics were washed with brine then dried over sodium sulfate, filtered and evaporated. The crude material was purified by chromatography on a 5 g silica II cartridge, eluting with 10-33% diethyl ether in pentane to afford hexahydro-[1,4]dioxino[2,3-b]pyridine-5-carboxylic acid tert-butyl ester as an off-white oil (0.106 g).

Provenance & Evidence