Reaktion #10444

Reaktionsgleichung

3-ethylidenepyrrolidine-1-carboxylic acid benzyl ester

3-Ethylidenepyrrolidine-1-carboxylic acid benzyl ester

3-chloroperoxybenzoic acid

sodium sulfite

→

title compound

Ausbeute 44.8%

2-Methyl-1-oxa-5-azaspiro[2,4]heptane-5-carboxylic acid benzyl ester

Ausbeute 44.8%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenThe organic layer is washed with 5% sodium bicarbonate solution
2. 2
   Trocknendried over Na2SO4
3. 3
   Sonstigeevaporated
4. 4
   SonstigeThe residue is purified by column chromatography (1:1 hexanes/ethyl acetate)

Vorschrift

A solution of 3-ethylidenepyrrolidine-1-carboxylic acid benzyl ester (Example A8, 0.65 g, 2.8 mmol) and 3-chloroperoxybenzoic acid (0.86 g, 5 mmol) in dichloromethane (15 mL) is stirred at room temperature for 3 hours. The excess peracid is decomposed by the addition of 10% sodium sulfite. The organic layer is washed with 5% sodium bicarbonate solution, dried over Na2SO4 and evaporated. The residue is purified by column chromatography (1:1 hexanes/ethyl acetate) to afford the title compound (0.310 g). 1H NMR (200 MHz, CDCl3): δ 7.36–7.26 (m, 5H), 5.14 (s, 2H), 3.73–3.55 (m, 3H), 3.34 (d. 1H), 3.20–3.13 (m, 1H), 2.26–2.11 (m, 1H), 1.90–1.62 (m, 1H), 1.33 (d, 3H).

Quelle