C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C@@:9]12[O:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[C@@H:10]1[CH2:11][N:12]([CH3:15])[CH2:13][CH2:14]2.C[S-].[Li+].Cl>CN(C)P(N(C)C)(N(C)C)=O.O>[OH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C@@:9]12[O:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[C@@H:10]1[CH2:11][N:12]([CH3:15])[CH2:13][CH2:14]2A mixture of 1.51 g of cis-1,2,3,4,4a,9b-hexahydro-4a-(2-methoxyphenyl)-2-methyl-benzofuro[3,2-c]pyridine and 1.56 g of lithium thiomethoxide in 13 ml of dry hexamethylphosphoramide was heated at 140° under a drying tube for 4 hours. The cooled reaction mixture was diluted with 150 ml of water and the pH adjusted to 7 by slow addition of 2N HCl with stirring. As the pH reached neutral, product started to precipitate out. The mixture was cooled to 0° and stirred for 30 minutes. The precipitated material was collected, washed with water and then a small amount of ether, and dried to afford 1.14 g (79.5%) of crystalline solid, m.p. s 178, 188°-191°. Recrystallization from ethanol gave 0.90 (62.7%) of colorless crystals, m.p. s 197, 197.5°-199°.
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