Reaktion #324478

Reaktionsgleichung

NaHCO3

azetidine-1,3-dicarboxylic acid mono-tert-butyl ester

O,N-dimethyl-hydroxylamine hydrochloride

triethylamine

HATU

→

title compound

Ausbeute 84.3%

3-(Methoxy-methyl-carbamoyl)-azetidine-1-carboxylic acid tert-butyl ester

Ausbeute 84.3%

Lösungsmittel

ethyl acetate

DMF

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe aqueous portion was extracted three times with ethyl acetate
2. 2
   TrocknenThe combined organic fractions were dried (Na2SO4)
3. 3
   Einengenconcentrated
4. 4
   Sonstigethe crude product was purified

Vorschrift

To a solution of azetidine-1,3-dicarboxylic acid mono-tert-butyl ester (3.5 g, 17 mmol) in DMF (50 mL) was added O,N-dimethyl-hydroxylamine hydrochloride (3.4 g, 34 mmol), triethylamine (9.6 mL, 69 mmol), HATU (13.4 g, 34.6 mmol) and DCM (125 mL). After stirring for 16 h, saturated NaHCO3 solution and ethyl acetate were added. The aqueous portion was extracted three times with ethyl acetate. The combined organic fractions were dried (Na2SO4) and concentrated and the crude product was purified using RP HPLC (basic conditions) to provide the title compound (3.5 g, 83%) MS (ESI): mass calcd. for C11H20N2O4, 244.1; m/z found, 189.1 [M-t-Bu]+. 1H NMR (CDCl3): 4.14-4.03 (m, 2H), 4.05 (t, J=8.7 Hz, 2H), 3.66 (s, 3H), 3.63-3.59 (m, 1H), 3.21 (s, 1H), 1.43 (s, 9H).

Quelle