Thionyl Chloride → Benzamide
반응식
[Si](OC1C=C(C=CC=1)C([C:14]1[CH:26]=[CH:25][C:17]([C:18]([N:20](CC)CC)=[O:19])=[CH:16][CH:15]=1)O)(C(C)(C)C)(C)C.S(Cl)(Cl)=O.C[C@H]1CN[C@H](C)CN1.O.[F-].C([N+](CC)(CC)CC)C>>[C:18]([NH2:20])(=[O:19])[C:17]1[CH:25]=[CH:26][CH:14]=[CH:15][CH:16]=1참가 물질
5
실험 절차
4-(3-(tert-Butyldimethylsilyloxy)-α-hydroxybenzyl)-N,N-diethylbenzamide (Example 1, infra) was treated with thionyl chloride and trans-2,5-dimethylpiperazine as described in Example 5. The crude mixture of diastereomers was purified by chromatography on silica gel (Waters Prep 500) with dichloromethane:ethanol:triethylamine (100:0.25:0.1). The less mobile isomer (1.28 g, 2.5 mmol) was dissolved in acetonitrile and treated with tetraethylammonium fluoride hydrate (0.6 g, 4.0 mmol) as in Example 7 to give 0.46 g of (±)-N,N-diethyl-4-((αR*)-3-hydroxy-α-((2R*, 5S*)-2,5-dimethyl-1-piperazinyl)benzyl)benzamide as a white solid, mp 175-177° C.