Tetrabutylammonium Fluoride → HCID 86760284, compound

Participants

Reaction Steps

A solution of 8.1 g (15.0 mmol) 1-{[(3R,4S)-3-(tert-butyldimethylsilyloxymethyl)-4-(3-fluorophenyl)pyrrolidin-1-yl]methyl}cyclohexanecarboxylic acid, benzyl ester (from Step A) in 150 mL of THF at 0° C. was treated with 45 mL of 1.0 M tetrabutylammonium fluoride solution in THF. The resulting mixture was warmed to rt and stirred for 20 h. The reaction mixture was partitioned between 200 mL of ether and 100 mL of 50% sat'd NaHCO3 and the layers were separated. The organic layer was dried over MgSO4 and concentrated. Purification by Biotage Flash 40 using a 40 M cartridge and 0.5 L to 1.0 L of 9:1 to 2:1 v/v hexane/ethyl acetate as the eluant afforded the title compound: 1H NMR (500 MHz, CDCl3) δ 1.23–3.68 (20H), 5.18 (ABq, J=12.3, 2H), 6.88–7.01 (3H), 7.21–7.40 (6H).

Provenance & Evidence