[4-(PYRROLIDIN-1-YLMETHYL)PHENYL]METHANOL synthesis

Yield:91271-60-2 84%

Reaction Conditions:

Stage #1: 4-Pyrrolidin-1-ylmethyl-benzoic acid methyl esterwith lithium aluminium tetrahydride in tetrahydrofuran at 0 - 20; for 1.5 h;
Stage #2: with water in tetrahydrofuran at 0; for 0.5 h;

Steps:

4-(Tetrahydro-1H-1-pyrrolylmethyl)phenyl]methanol (8a).; To a stirred solution of LAH (0.5 g, 14.21 mmol) in dry THF (10 ml_) at 0 ⁰C was added dropwise solution of 7a (1.55 g, 7.105 mmol) in 5 ml_ dry THF. The mixture was stirred at room temperature for 1.5 h and then cooled to 0 ⁰C. The solution was then quenched by adding cold water (4 ml_) and the resulting suspension was stirred for 30 min, diluted with ether, filtered through celite and concentrated under reduced pressure. The residue was dissolved in EtOAc and the solution was washed with H₂O, organic layer was dried over Na₂SO₄ and concentrated in vacuo. The crude material was purified by column chromatography (CH₂CI₂/MeOH/NH₄OH 9:1 :0.01 ) to give 8a as an oil (1.1 g, 84%); ¹H NMR (CDCI₃): δ 7.33-7.24 (m, 4H), 4.63 (s, 2H), 3.59 (s, 2H), 2.52-2.46 (m,5H), 1.79-1.72 (m, 4H); ESI MS m/z (M+1)⁺ 192.

References:

WO2007/104695,2007,A1 Location in patent:Page/Page column 27-29