Propyl mercaptan → HCID 11833689, compound

Participants

Reaction Steps

To a stirred solution of NaH (60% dispersion in mineral oil) (0.483 g, 12.075 mmol) in DMF under nitrogen at RT was added propanethiol (1.09 ml, 12.07 mmol) and the mixture stirred for 30 min. A solution of (R)-(+)-4-[2-(3-cyclopentyloxy-4-methoxyphenyl)-2-phenylethyl]pyridine (made as described in WO 94/14742) (1.8 g, 4.83 mmol) in DMF was added, the mixture heated to reflux for 5 h, allowed to cool (the reaction was followed by tic) and concentrated in vacuo. The residue was taken up in CH2Cl2 and washed with aqueous NaHCO3 solution. The aqueous phase was extracted with CH2Cl2, the combined organic phase dried (MgSO4), filtered and concentrated in vacuo. The residue was subjected to chromatography (SiO2 ; Et2O) then recrystallised (i-propylether) to give the title compound (6.00 g) as a white solid. m.p. 158°-159° C. (Found C, 79.37; H, 6.96; N, 3.66. C24H25O2N requires C, 80.19; H, 7.01; N, 3.90%). δH (CDCl3) 1.5-1.9 (8H, m, (CH2)4), 3.39 (2H, dd, J 8, 1 Hz, CH2 pyridine), 4.12 (1H, t, J 8 Hz, CHCH2), 4.62 (1H, m, OCH), 5.52 (1H, br s, OH), 6.57 (1H, m, C6H3), 6.6-6.7 (1H, m, C6H3), 6.75-6.8 (1H, m, C6H3), 6.91 (2H, d, J 6. Hz, H3, H5 pyridine), 7.1-7.3 (5H, m, C6H5), and 8.38 (2H, d, J 6 Hz, H2, H6 pyridine).

Provenance & Evidence