Reaktion #1546898

Reaktionsgleichung

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

trifluoroacetic acid

→

title compound

Ausbeute 77.3%

(3R)-3-[(Benzylthio)methyl]pyrrolidine

Ausbeute 77.3%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigebefore quenching with anhydrous methanol (2 ml)
2. 2
   Sonstigeevaporating in vacuo
3. 3
   workup.ADDITIONMore methanol (2 ml) was added to the residue
4. 4
   Sonstigeremoved in vacuo
5. 5
   workup.DISSOLUTIONThe residual oil was then dissolved in dichloromethane (25 ml)
6. 6
   Waschenwashed with 2N NaOH solution (10 ml)
7. 7
   Waschenthe combined dichloromethane extracts were washed with saturated NaCl solution (10 ml)
8. 8
   Trocknendried (Na2SO4)
9. 9
   Sonstigeevaporated in vacuo
10. 10
    SonstigeThe residue was purified by flash chromatography (silica gel, CH2Cl2 /MeOH/NH3, 85:15:1.5)

Vorschrift

To a stirred solution of (3R)-3-(benzylthio)methyl-1-(tert-butoxycarbonyl)pyrrolidine (0.2320 g, 0.755 mmol) in dichloromethane (3 ml), under argon, was added trifluoroacetic acid (1 ml) and the mixture was stirred at room temperature for 65 minutes before quenching with anhydrous methanol (2 ml) and evaporating in vacuo. More methanol (2 ml) was added to the residue and removed in vacuo. The residual oil was then dissolved in dichloromethane (25 ml) and washed with 2N NaOH solution (10 ml). The aqueous layer was reextracted with more dichloromethane (15 ml) and the combined dichloromethane extracts were washed with saturated NaCl solution (10 ml), dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography (silica gel, CH2Cl2 /MeOH/NH3, 85:15:1.5) to give 0.1210 g (77%) of the title compound as a colourless oil. δH (250 MHz,CDCl3) 1.41 (1H, m), 1.90-2.00 (1H, m), 2.24 (1H, m), 2.42-2.50 (2H, m), 2.57 (1H, dd, J=6.5 and 11.0 Hz), 2.82-2.99 (2H, m), 3.07 (1H, dd, J=7.3 and 11.0 Hz), 3.72 (2H, s), 7.20-7.36 (5H, m); m/e (ES) 208 (M+ +1).

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