Реакция #10454

Уравнение реакции

diethyl azodicarboxylate

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

triphenylphosphine

phthalimide

→

title compound

Выход 21.9%

2-(1-Benzyl-3-methoxymethylpyrrolidin-3-ylmethyl)isoindole-1,3-dione

Выход 21.9%

Растворители

tetrahydrofuran

Условия реакции

Обработка

1. 1
   Другоеis cooled to 0° C.
2. 2
   Концентрированиеconcentrated under vacuum
3. 3
   ДругоеThe residue is purified by flash column chromatography (1:5 ethyl acetate/hexanes)

Методика

A solution of (1-benzyl-3-methoxymethylpyrrolidin-3-yl)methanol (Example A19, 1.71 g, 7.27 mmol), triphenylphosphine (2.16 g, 8.22 mmol), phthalimide (1.14 g, 7.73 mmol), and anhydrous tetrahydrofuran is cooled to 0° C. and treated with diethyl azodicarboxylate (1.62 g, 9.31 mmol). The resulting mixture is stirred at room temperature for 18 hours and concentrated under vacuum. The residue is purified by flash column chromatography (1:5 ethyl acetate/hexanes) to afford the title compound, (0.58 g) as a solid. 1H NMR (200 MHz, CDCl3): δ 7.91–7.80 (m, 2H), 7.78–7.66 (m, 2H), 7.39–7.11 (m, 5H), 3.95–3.72 (m, 2H), 3.65–3.40 (m, 2H), 3.31 (s, 2H), 3.27 (s, 3H), 2.72–2.34 (m, 4H), 2.02–1.82 (m, 1H), 1.76–1.56 (m, 1H). MS ES: m/z 365 (MH+).

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