Dichloromethane → (2S)-1-(3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl) amino-3-phenylthio-2-propanol hydrochloride

HRID 2299683Notes

Reaction equation

HRID 2299683 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]=1

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 2733225Ytterbium triflateHCID 12347320(2S)-1-phenylthio-2,3-epoxypropaneHCID 180073203-methoxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-6-amine

Product 1

HCID 69330155(2S)-1-(3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl) amino-3-phenylthio-2-propanol hydrochloride

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

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (chloroform:methanol=50:1 to 20:1)

Sources & evidence

ORD record
ord-ab7f8a8fe9f740079069eb958bbe3d0b
Source dataset
uspto-grants-2002_12
Patent number
US06495546B1

Reaction notes

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