Dimethylformamide → HCID 58826433, compound

Participants

Reaction Steps

To a stirred, cooled (0° C.) solution of (1R,3S,4S)-3-azido-4-hydroxy-cyclopentanecarboxylic acid methyl ester (300 mg; CAS 213742-85-9) in DMF (5 ml) under an argon atmosphere was added NaH (78 mg; 55% dispersion in mineral oil). The ice bath was removed and stirring at r.t. was continued for 1 h. The mixture was cooled again and methyl iodide (0.3 ml) was added in one portion. The mixture (slowly warming up to r.t.) was then stirred for 18 h. More methyl iodide (0.3 ml) was added and the mixture (orange slurry) was stirred at r.t. for another 7 h. More methyl iodide (0.3 ml) was added and stirring was continued for another 17 h. The mixture was diluted with EtOAc and washed with H2O (10 ml). The aqueous phase was back extracted with EtOAc. The combined organics were washed with H2O and brine, dried (MgSO4), filtered and concentrated. The crude product was purified by column chromatography (silica gel; gradient: cyclohexane→cyclohexane/EtOAc 65:35) to give (3S,4S)-3-azido-4-methoxy-cyclopentanecarboxylic acid methyl ester (215 mg, epimeric mixture) as light yellow oil. MS: 200.3 ([M+H]+).

Provenance & Evidence