Reaction Steps
Pd/C at 10% (290 mg) is suspended in a solution of (S)-1-(4-benzyloxyphenoxy)-2-hydroxy-3-[4-(4-methoxyphenylsulfonyl)piperazin-1-yl)propane (Example 26) (583 mg, 1.14 mM) in CH2Cl2 (10 ml) and maintained in agitation in H2 atmosphere (1 atm) for 18 hours. The catalyst is then removed by filtering the reaction mixture on Celite, and the solvent is distilled under vacuum. The oily residue is crystallized (ethyl acetate/petroleum ether). A white solid is obtained (90% of yield). Pf 148.3-149.2° C.s. [α]D=−7.6 (c 1.07, CHCl3). FT-IR (KBr): 3466, 3050, 2969, 2941, 2921, 2896, 2864, 1593, 1576, 1511, 1468, 1458, 1445, 1348, 1328, 1306, 1254, 1234, 1200, 1177, 1165, 1136, 1101, 1051, 1017, 946, 833, 804, 737 cm−1. 1NMRs (500 MHz CD3OD, δ): 7.90-7.80 (bs, 1H, OH); 7.71-7.68 (m, 2H, aromatic protons); 7.13-7.10 (m, 2H, aromatic protons); 6.75-6.73 (m, 2H, aromatic protons); 6.68-6.66 (m, 2H, aromatic protons); 4.00-3.98 (m, 1H, CHOH), 3.88 (s, 3H, OCH3), 3.86-3.83 (dd, 1H, J=9.7 and 4.4 Hz, CH2OAr); 3.80-3.77 (dd, 1H, J=9.7 and 5.9 Hz, CH2OAr); 3.70-3.50 (bs, 1H, OH); 2.98 (m, 4H, 2 CH2N of piperazine); 2.60 (m, 4H, 2 CH2 of piperazine); 2.55-2.52 (dd, 1H, J=13.0 and 4.8 Hz, CHOHCH2N); 2.50-2.46 (dd, 1H, J=13.0 and 7.5 Hz, CHOHCH2N). 13C NMRs (75 MHz CD3OD, δ): 163.72, 152.47, 150.31, 129.97, 126.98, 115.60, 115.55, 114.25, 71.35, 67.31, 60.45, 55.08, 52.81, 46.07. MS-ESI m/z (%): 445 [M+Na]+ (100). MS-MS (445): 445(100), 335 (69), 292 (54), 279 (13), 250 (8), 222 (32). Anal. Calc. for C20H26N2O5S: C, 56.86; H, 6.20; N, 6.63. Found: C, 57.03; H, 6.16; N, 6.66.
