Реакция #986894

Уравнение реакции

(1-benzyl-pyrrolidin-3-yl)-methanol

vinyl chloroformate

→

oil

Выход 71.0%

Carbonic Acid 1-benzyl-pyrrolidin-3-ylmethyl ester vinyl ester

Выход 71.0%

Растворители

1,2-dichloroethane

Условия реакции

Обработка

1. 1
   Температураto reflux for 2 h
2. 2
   Концентрированиеthen concentrated in vacuo
3. 3
   ДругоеPurification of the crude material by column chromatography on silica gel (5% MeOH/CH2Cl2)

Методика

A solution of (1-benzyl-pyrrolidin-3-yl)-methanol (prepared as described by Y.-H. Wu and R. F. Feldkamp, Pyrrolidines I, 1961, 26, 1519-1524) (455 mg, 2.38 mmol) and vinyl chloroformate (0.40 mL, 4.7 mmol) in 1,2-dichloroethane (10 mL) was heated to reflux for 2 h then concentrated in vacuo. Purification of the crude material by column chromatography on silica gel (5% MeOH/CH2Cl2) gave a yellow oil (440 mg, 71%). 1H NMR (CDCl3) δ 1.84 (m, 1H), 2.26 (m, 1H), 3.03 (m, 5H), 4.01 (br s, 2H), 4.23 (m, 2H), 4.61 (dd, 1H, J=6.2, 2.3 Hz), 4.93 (dd, 1H, J=14, 2.1 Hz), 7.06 (dd, 1H, J=14, 6.3 Hz), 7.41 (m, 3H), 7.53 (m, 2H).

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