Reacción #10454

Ecuación de reacción

diethyl azodicarboxylate

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

triphenylphosphine

phthalimide

→

title compound

Rendimiento 21.9%

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

Rendimiento 21.9%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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+).

Fuente