反応 #10454

反応方程式

diethyl azodicarboxylate

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

triphenylphosphine

phthalimide

→

title compound

収率 21.9%

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

収率 21.9%

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   その他is cooled to 0° C.
2. 2
   濃縮concentrated under vacuum
3. 3
   その他The residue is purified by flash column chromatography (1:5 ethyl acetate/hexanes)

実験手順

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+).

出典