[ClH:1].[CH3:2][N:3]([CH2:5][CH:6]1[C:20](=[O:21])[C:10]2[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:12][O:13][C:9]=2[CH2:8][CH2:7]1)[CH3:4].[BH4-].[Na+].Cl.C(=O)(O)[O-].[Na+]>C(O)C.Cl.CCOCC.CCOCC>[ClH:1].[CH3:4][N:3]([CH2:5][C@@H:6]1[C@H:20]([OH:21])[C:10]2[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:12][O:13][C:9]=2[CH2:8][CH2:7]1)[CH3:2]6,7-Dihydro-5-dimethylaminomethyl-3-phenyl- 1,2-benzisoxazol-4(5H)-one hydrochloride (7.5 g) was dissolved in 100 ml ethanol and treated with 5.0 g sodium borohydride. After stirring for 1 hour the reaction mixture was distributed between 5% HCl and ether. The aqueous phase was then made basic with solid sodium bicarbonate and extracted with ether. Concentration under reduced pressure gave the product as a mixture of trans and cis isomers which was chromatographed by preparative high pressure liquid chromatography (HPLC) (ethyl acetate/CH3CN/diethylamine; 90:10:1) to give 2.20 g of the pure cis isomer. The hydrochloride was formed in HCl/ether and then recrystallized from methanol/ether to give 1.81 g of cis-5-(dimethylaminomethyl)-4-hydroxy-3-phenyl-4,5,6,7-tetrahydro-1,2-benzisoxazole hydrochloride, m.p. 235°-236° C.
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