Acetone → Rac-3-{4-[5-(5-diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-propane-1,2-diol

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Reaction Steps

{5-[3-(4-Allyl-phenyl)-[1,2,4]oxadiazol-5-yl]-3-methyl-thiophen-2-ylmethyl}-diethyl-amine (625 mg) is obtained as a yellow oil starting from 5-diethylaminomethyl-4-methyl-thiophene-2-carboxylic acid (1.50 g, 6.60 mmol) and 4-allyl-N-hydroxy-benzamidine (1.28 g, 7.26 mmol) according to Method A; LC-MS: tR=0.64 min; [M+1]+=368.20. b) To a solution of {5-[3-(4-allyl-phenyl)-[1,2,4]oxadiazol-5-yl]-3-methyl-thiophen-2-ylmethyl}-diethyl-amine (550 mg, 1.50 mmol) in acetone (7.5 mL) and water (0.5 mL), OsO4 (38 mg, as a 2.5% solution in butanol) followed by N-methyl morpholine-N-oxide (243 mg, 1.80 mmol) is added. The mixture is stirred at rt for 16 h. The clear yellow solution is diluted with DCM, washed with water (3×50 mL), dried over MgSO4, filtered, concentrated and dried to give crude title compound (619 mg) as yellow oil; LC-MS: tR=0.48 min; [M+1]+=401.70; 1H NMR (CDCl3): δ1.11 (t, J=7.0 Hz, 6H), 2.25 (s, 3H), 2.63 (q, J=7.3 Hz, 4H), 2.84-2.92 (m, 2H), 3.55 (dd, J=11.0, 7.0 Hz, 1H), 3.69-3.76 (m, 4H), 3.96-4.04 (m, 1H), 7.37 (d, J=7.8 Hz, 2H), 7.66 (s, 1H), 8.08 (d, J=7.8 Hz, 2H).

Provenance & Evidence