Reaktion #1546903

Reaktionsgleichung

(3R)-3-(benzylthio)methyl-1-(tert-butoxycarbonyl)pyrrolidine

3-chloroperoxybenzoic acid

NaHCO3

→

title compound

Ausbeute 89.0%

(3R)-3-(Benzylsulfinyl)methyl-1-(tert-butoxycarbonyl)pyrrolidine

Ausbeute 89.0%

Lösungsmittel

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe organic layer was separated
2. 2
   Waschenwashed with more 5% NaHCO3 solution (15 ml)
3. 3
   Trocknensaturated NaCl solution (10 ml), dried (MgSO4)
4. 4
   Sonstigeevaporated in vacuo
5. 5
   SonstigeThe residue was purified by flash chromatography (silica gel, 3% MeOH/CH2Cl2)

Vorschrift

To a stirred solution of (3R)-3-(benzylthio)methyl-1-(tert-butoxycarbonyl)pyrrolidine (0.2553 g, 0.830 mmol) in ethyl acetate (15 ml), under argon, cooled in a bath at ca. -40° C., was added portionwise 57-86% 3-chloroperoxybenzoic acid (0.2094 g). The mixture was then allowed to warm to 0° C. over 1.5 h, before pouring into 5% NaHCO3 solution (15 ml). The organic layer was separated and washed with more 5% NaHCO3 solution (15 ml), then saturated NaCl solution (10 ml), dried (MgSO4) and evaporated in vacuo. The residue was purified by flash chromatography (silica gel, 3% MeOH/CH2Cl2) to give 0.2381 g (89%) of the title compound as a colourless oil. δH (250 MHz, CDCl3) 1.44 (9H, s), 1.61 (1H, m), 2.15 (1H, m), 2.52 (1H, m), 2.66 (2H, m), 3.00 (1H, m), 3.29 (1H, m), 3.43 (1H, m), 3.63 (1H, m), 3.96 (1H, d, J=12.9 Hz), 4.07 (1H, d, J=12.9 Hz), 7.28-7.30 (2H, m), 7.35-7.39 (3H, m). m/e (ES+) 324 (M+H)+.

Quelle