Sodium Bicarbonate → (2S)-1-[N-benzyl-N-(3-isopropoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)-amino]-3-phenoxy-2-propanol

HRID 1351873ノート

反応式

HRID 1351873 の反応式
[CH2:1]([NH:8][CH:9]1[CH2:15][CH2:14][CH2:13][C:12]2[CH:16]=[CH:17][C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[CH:19][C:11]=2[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:24]([CH2:31][C@H:32]1[O:34][CH2:33]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=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+]>ClCCl>[CH2:1]([N:8]([CH2:33][C@H:32]([OH:34])[CH2:31][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH:9]1[CH2:15][CH2:14][CH2:13][C:12]2[CH:16]=[CH:17][C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[CH:19][C:11]=2[CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 516892Sodium BicarbonateHCID 1534345(2S)-2-(phenoxymethyl)oxiraneHCID 2733225Ytterbium triflateHCID 18007411N-benzyl-(3-isopropoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amine

生成物 1

HCID 57196896(2S)-1-[N-benzyl-N-(3-isopropoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)-amino]-3-phenoxy-2-propanol収率 79.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Under nitrogen, to a solution of N-benzyl-(3-isopropoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amine (258 mg) and (2S)-3-phenoxy-1,2-epoxypropane (138 mg) in dichloromethane (5 ml) was added ytterbium(III) trifluoromethanesulfonate (52 mg) at room temperature, and the mixture was stirred at the same temperature for 60 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 (hexane:ethyl acetate=10:1 to 5:1) to give (2S)-1-[N-benzyl-N-(3-isopropoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)-amino]-3-phenoxy-2-propanol (303 mg).

後処理

  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 (hexane:ethyl acetate=10:1 to 5:1)

出典と根拠

ORDレコード
ord-206c0b1847e6462b94d4e99002e67f5d
出典データセット
uspto-grants-2007_05
特許番号
US07217706B2

反応ノート

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