Hydroxyamine hydrochloride → HCID 20712351, compound

Participants

Reaction Conditions

Reaction Steps

5-(4-Benzyloxy-benzenesulfonyl)-1-methyl-2-oxa-5-aza-bicyclo[2.2.2]octan-3-one (0.035 g, 0.09 mmol) was dissolved in 0.80 mL of a 0.81 M solution of hydroxylamine in methanol (prepared by treating 7.25 mL of a 0.81 M solution of sodium methoxide in methanol with 0.52 g of hydroxylamine hydrochloride). The resulting mixture was shaken at 60° C. for 10 minutes. After cooling to room temperature, the mixture was diluted with 1M HCl, extracted twice with ethyl acetate, and the combined organic layers were washed twice with 50% saturated aqueous NaHCO3, once with 1M pH 7.0 phosphate buffer, dried over Na2SO4, filtered and concentrated in vacuo. Trituration of the residue with CH2Cl2-hexane afforded 0.027 g of 1-(4-benzyloxy-benzenesulfonyl)-5-hydroxy-5-methyl-piperidine-2-carboxylic acid hydroxyamide as a colorless solid:

Provenance & Evidence