Hydroxyamine hydrochloride → HCID 178452026, compound

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([C:13]#[N:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:16][OH:17].C([O-])(O)=O.[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([C:13](=[NH:14])[NH:16][OH:17])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Procedure

(R)-3-Cyano-pyrrolidine-1-carboxylic acid tert-butyl ester (1.02 g, 5.2 mmol), hydroxylamine hydrochloride (396 mg, 5.7 mmol) and NaHCO3 (487 mg, 5.8 mmol) were added to MeOH (12 mL) and the solution was heated to reflux. After 4 h, the reaction was concentrated in vacuo. The residue was partitioned between EtOAc and brine. The layers were separated and the organic layer was dried over Na2SO4, filtered and concentrated to yield 927 mg of crude (R)-3-(N-hydroxycarbamimidoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester as a yellow foam.