Reaktion #1464953

Reaktionsgleichung

trans-3-(3-cyclopentoxy-4-methoxyphenyl)-4-(methoxycarbonyl)pyrrolidine

isopropyl chloroformate

toluene

→

trans-3-(3-cyclopentoxy-4-methoxyphenyl)-4-methoxycarbonyl-1-(methylethoxycarbonyl)pyrrolidine

Ausbeute 44.0%

Lösungsmittel

CH2Cl2

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with 1M H3PO4
2. 2
   TrocknenThe organic layer was dried over MgSO4
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated under reduced pressure

Vorschrift

To a solution of trans-3-(3-cyclopentoxy-4-methoxyphenyl)-4-(methoxycarbonyl)pyrrolidine (500 mg, 1.57 mmol) in 4 mL of CH2Cl2 was added at 0° C. 4-dimethylaminopyridine (250 mg, 2.04 mmol), followed by isopropyl chloroformate (1.7 mL of a 1M toluene solution). After 16 hr the reaction was diluted with CH2Cl2 and washed with 1M H3PO4. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. Silica gel chromatography (2:1, hexanes:ethyl acetate) provided trans-3-(3-cyclopentoxy-4-methoxyphenyl)-4-methoxycarbonyl-1-(methylethoxycarbonyl)pyrrolidine as a white solid (280 mg, 44%). Anal. Calcd for C22H29NO6 : C, 65.17; H, 7.71; N, 3.45. Found: C, 65.16; H, 7.69; N, 3.43.

Quelle