Dichloromethane → (2S)-1-(3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl) amino-3-phenylthio-2-propanol hydrochloride
Reaction equation
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[CH2:7][CH2:8][CH2:9][CH:10]([NH2:12])[CH2:11][C:5]=2[CH:4]=1.[C:15]1([S:21][CH2:22][C@H:23]2[O:25][CH2:24]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.FC(F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O.C(=O)([O-])O.[Na+].[Cl:56]CCl>>[ClH:56].[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[CH2:7][CH2:8][CH2:9][CH:10]([NH:12][CH2:24][C@H:23]([OH:25])[CH2:22][S:21][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:11][C:5]=2[CH:4]=1Participants
Reactant 5
Product 1
Procedure
Under nitrogen, to a solution of 3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-ylamine (330 mg) and (2S)-1-phenylthio-2,3-epoxypropane (290 mg) in dichloromethane (5 ml) was added ytterbium(III) trifluoromethanesulfonate (110 mg) at room temperature, and the mixture was stirred at the same temperature for 24 hours. The resulting mixture was poured into saturated aqueous sodium hydrogencarbonate and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (chloroform:methanol=50:1 to 20:1) followed by treatment with 4N hydrogen chloride in ethyl acetate to give (2S)-1-(3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amino-3-phenylthio-2-propanol hydrochloride (360 mg).
Workup
- extractionextracted with ethyl acetate
- washThe organic layer was washed with brine
- dry with materialdried over anhydrous magnesium sulfate
- customevaporated in vacuo
- customThe residue was purified by column chromatography on silica gel (chloroform:methanol=50:1 to 20:1)
Sources & evidence
- ORD record
- ord-0dea245d67624273b8395928ad8267c6
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07217706B2
Reaction notes
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