Hydroxyamine hydrochloride → HCID 58504342, compound

Reaction equation

[C:1]([C:3]1[CH:17]=[CH:16][C:6]([CH2:7][N:8]2[CH2:11][CH:10]([C:12]([O:14][CH3:15])=[O:13])[CH2:9]2)=[CH:5][CH:4]=1)#[N:2].Cl.[NH2:19][OH:20].C(=O)(O)[O-].[Na+]>CO>[OH:20]/[N:19]=[C:1](/[C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH2:9][CH:10]([C:12]([O:14][CH3:15])=[O:13])[CH2:11]2)=[CH:16][CH:17]=1)\[NH2:2]

Participants

Procedure

A mixture of methyl 1-(4-cyanobenzyl)azetidine-3-carboxylate (760 mg, 3.30 mmol), hydroxylamine hydrochloride (459 mg, 6.60 mmol) and sodium bicarbonate (1109 mg, 13.20 mmol) in MeOH (4.9 mL) was heated to reflux for 2.5 hr. After cooling to rt, the reaction mixture was filtered and the filtrate was concentrated to a residue that was partitioned between EtOAc (75 mL) and water (50 mL). The aqueous layer was extracted with EtOAc (75 mL) and the combined organic layers were dried (MgSO4) and concentrated to afford (Z)-methyl 1-(4-(N′-hydroxycarbamimidoyl)benzyl)azetidine-3-carboxylate (470 mg, 1.785 mmol) as a colorless foam. MS:(M+H)=264.28. 1H NMR (400 MHz, CDCl3) δ ppm 3.30-3.39 (m, 3H) 3.54 (m, 2H) 3.64 (s, 2H) 3.71 (s, 3H) 4.86 (brs, 2H) 7.31 (d, J=8.3 Hz, 2H) 7.57 (d, J=8.3 Hz, 2H).