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

HRID 1936963ノート

反応式

HRID 1936963 の反応式
[O:1]([CH2:8][C@H:9]1[O:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:12]([NH:19][CH:20]1[CH2:26][CH2:25][CH2:24][C:23]2[C:27]([OH:31])=[CH:28][CH:29]=[CH:30][C:22]=2[CH2:21]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.FC(F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O>ClCCl>[CH2:12]([N:19]([CH:20]1[CH2:26][CH2:25][CH2:24][C:23]2[C:27]([OH:31])=[CH:28][CH:29]=[CH:30][C:22]=2[CH2:21]1)[CH2:10][C@H:9]([OH:11])[CH2:8][O:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参加物

5

反応物 3

HCID 1534345(2S)-2-(phenoxymethyl)oxiraneHCID 2733225Ytterbium triflateHCID 22462907N-benzyl-(1-hydroxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amine

生成物 1

HCID 70132831(2S)-1-[N-benzyl-(6,7,8,9-tetrahydro-1-hydroxy-5H-benzocyclohepten-6-yl)amino]-3-phenoxy-2-propanol収率 89.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A suspension of (2S)-3-phenoxy-1,2-epoxypropane (300 mg) (IL FARMACO, 50 (10), 643 (1995)), N-benzyl-(1-hydroxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amine (535 mg), and ytterbium(III) trifluoromethanesulfonate (372 mg) in dichloromethane (15 ml) was stirred at room temperature for 3 days and partitioned between ethyl acetate and aqueous sodium bicarbonate. The organic layer was separated, washed with brine, dried over sodium sulfate, and evaporated in vacuo. The residue was chromatographed (dichloromethane-methanol) over silica gel (16 g) to afford (2S)-1-[N-benzyl-(6,7,8,9-tetrahydro-1-hydroxy-5H-benzocyclohepten-6-yl)amino]-3-phenoxy-2-propanol (747 mg) as a colorless oil.

後処理

  1. custompartitioned between ethyl acetate and aqueous sodium bicarbonate
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. customThe residue was chromatographed (dichloromethane-methanol) over silica gel (16 g)

出典と根拠

ORDレコード
ord-4696756b08da4dec8ce0e7fcb5616f7d
出典データセット
uspto-grants-2002_05
特許番号
US06391915B2

反応ノート

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