Trifluoroacetic acid → methyl 4-[5-(R)-phenyl-2-(S)-pirrolidinylmethoxy]benzate

HRID 354441ノート

反応式

HRID 354441 の反応式
C([N:8]1[C@@H:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:11][CH2:10][C@H:9]1[CH2:19][O:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=1)(OC(C)(C)C)=O.FC(F)(F)C(O)=O>C(Cl)Cl>[C:13]1([C@@H:12]2[NH:8][C@H:9]([CH2:19][O:20][C:21]3[CH:22]=[CH:23][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:29][CH:30]=3)[CH2:10][CH2:11]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 20737850HCID 20737850、化合物

生成物 1

HCID 69332954methyl 4-[5-(R)-phenyl-2-(S)-pirrolidinylmethoxy]benzate収率 37.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of methyl 4-[N-Boc-5-(R)-phenyl-2-(S)-pyrrolidinylmethoxy]benzoate (1.28 g, 3.11 mmol) in CH2Cl2 (30 ml) was added trifluoroacetic acid (10 ml) at rt, and the resulting mixture was stirred for 45 min. The mixture was concentrated in vacuo and poured into aq.NaHCO3, then extracted with CHCl3. The organic layer was washed with water, drying over anhydrous Na2SO4, and concentrated in vacuo to give methyl 4-[5-(R)-phenyl-2-(S)-pirrolidinylmethoxy]benzate (363 mg, quant.) as yellowish oil. The product was used for next reactions without further purification. 1H-NMR (CDCl3) δ1.71-1.83 (m, 2 H), 2.03-2.10 (m, 1 H), 2.15-2.24 (m, 1 H), 3.68-3.74 (m, 1 H), 3.89 (s, 3 H), 4.01-4.09 (m, 2 H), 4.28 (t, J=7.2 Hz, 1 H), 6.95 (d, J=8.8 Hz, 2 H), 7.22-7.27 (m, 1 H), 7.33 (t, J=8.0 Hz, 2 H), 7.42 (d, J=7.6 Hz, 2 H), 8.00 (d, J=8.8 Hz, 2 H); MS (ESI) m/z, 312 (M++H) 353 (M++CH3CN).

後処理

  1. concentrationThe mixture was concentrated in vacuo
  2. additionpoured into aq
  3. extractionNaHCO3, then extracted with CHCl3
  4. washThe organic layer was washed with water
  5. dry with materialdrying over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-1f8386478a6240b69e75b399ec420c7a
出典データセット
uspto-grants-2004_06
特許番号
US06756378B2

反応ノート

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