N,O-Dimethylhydroxylamine → Tert-butyl 2-(methoxy(methyl)carbamoyl)morpholine-4-carboxylate

Participants

Reaction Steps

Commercially available 4-(tert-butoxycarbonyl)morpholine-2-carboxylic acid (1.95 g, 8.43 mmol), 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (1.94 g, 10.1 mmol) and 1-hydroxybenztriazole monohydrate (1.25 g, 9.28 mmol) were combined in DMF (10 mL) and stirred at rt for 15 min. before adding N,O-dimethylhydroxylamine (0.987 g, 10.1 mmol), The reaction was stirred at rt overnight. The reaction was then concentrated and partitioned between saturated NaHCO3 and 20% isopropanol in CHCl3. The organic layer was dried (MgSO4) and concentrated. The crude residue was pulled through a layer of silica using CH2Cl2 and the eluting solvent. A colorless oil was isolated (0.7 g, 30%). 1H-NMR (DMSO-d6) δ 4.31-4.18 (bs, 1 H), 3.94-3.78 (m, 2 H), 3.76-3.61 (m, 4 H), 3.48 (dt, J1=11 Hz, J2=2.7 Hz, 1 H), 3.19-2.80 (m, 5 H), 1.39 (s, 9 H).

Provenance & Evidence