1-Chloroethyl chloroformate → HCID 9867172, compound

Participants

Reaction Steps

α-Chloroethyl chloroformate (95 μl) was added to a solution of 5-[(1-benzyl-4-piperidyl)oxymethyl]-3-[(2S)-1-cyclohexylmethylsulfonyl-2-piperidyl]-1,2,4-oxadiazole (325 mg) [see Example 16] in dichloromethane (20 ml) at 0° C. The reaction mixture was stirred for 1.5 hours after which time the dichloromethane was removed under reduced pressure and the residue dissolved in methanol. The mixture was then heated under reflux for 2 hours, the solvent removed under reduced pressure and the residue partitioned between diethyl ether and 2N aqueous hydrochloric acid solution. The aqueous layer was washed twice with diethyl ether and then neutralised (pH7) with sodium hydrogen carbonate. The aqueous layer was extracted with ethyl acetate, dried over magnesium sulphate and the solvent removed under reduced pressure to afford 3-[(2S)-1-cyclohexylmethylsulfonyl-2-piperidyl]-5-[4-piperidyloxymethyl]-1,2,4-oxadiazole (170 mg) as a brown oil.

Provenance & Evidence