Water → [1-Benzyl-4-(hydroxymethyl)pyrrolidin-3-yl]methanol

To a cooled (0° C.) solution of 1-benzyl-pyrrolidine-3,4-dicarboxylic acid dimethyl ester (8.66 g, 31.2 mmol) in THF (40 mL) was added LAH (2 M in THF, 62 mL, 62 mmol) over a ten minute period. The reaction mixture was stirred while warming (rt, 17 h). The reaction mixture was then cooled (0° C.), and stirred (15 min), and slowly treated sequentially with an addition of H2O (2.8 mL), 2 M NaOH (4.3 mL), and H2O (8.5 mL). The reaction mixture was then heated to reflux (64° C., 1 h). The reaction mixture was cooled and filtered through Celite® and the solid was washed with EtOAc. The filtrate was concentrated in vacuo to afford the title compound as a yellow oil (7.89 g, 100%). 1H NMR (500 MHz, CDCl3): 7.38-7.21 (m, 5H), 3.84-3.70 (m, 4H), 3.65-3.59 (m, 2H), 2.70-2.58 (m, 4H), 2.58-2.47 (m, 2H).

1. temperatureThe reaction mixture was then cooled (0° C.)
2. stirringstirred (15 min)
3. temperatureThe reaction mixture was then heated
4. temperatureto reflux (64° C., 1 h)
5. temperatureThe reaction mixture was cooled
6. filtrationfiltered through Celite®
7. washthe solid was washed with EtOAc
8. concentrationThe filtrate was concentrated in vacuo

ORD record

ord-c04466358b3f4a7d8d0cd7d03bf8e5a8

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08399465B2