Trifluoroacetic acid → methyl 4-[(2S,4S)-4-methoxy-2-pyrrolidinyl]methoxybenzoate

HRID 350492ノート

反応式

HRID 350492 の反応式
C(OC([N:8]1[CH2:12][C@@H:11]([O:13][CH3:14])[CH2:10][C@H:9]1[CH2:15][O:16][C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:14][O:13][C@@H:11]1[CH2:12][NH:8][C@H:9]([CH2:15][O:16][C:17]2[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=2)[CH2:10]1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 16093620HCID 16093620、化合物

生成物 1

HCID 16093585methyl 4-[(2S,4S)-4-methoxy-2-pyrrolidinyl]methoxybenzoate収率 99.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of methyl 4-[(2S,4S)-1-tert-butoxycarbonyl-4-methoxy-2-pyrrolidinyl]methoxybenzoate (2.38 g, 3.61 mmol) in CH2Cl2 (46 ml) was added TFA (23 ml) at room temperature. After 14 h stirring, the mixture was concentrated in vacuo. The residue was diluted by the addition of CH2Cl2 and 1 N NaOH, and extracted with CH2Cl2. The combined extracts were washed with brine, dried over Na2SO4, which was concentrated in vacuo. The residue was chromatographed on silica gel [50 g, CHCl3/MeOH (20/1)], to give methyl 4-[(2S,4S)-4-methoxy-2-pyrrolidinyl]methoxybenzoate (950 mg, 99%) as a yellow oil. 1H-NMR (CDCl3) δ 2.16 (t, J=5.3 Hz, 1H), 2.72 (s, 1H), 2.95 (d, J=6.8 Hz, 1H), 3.11 (d, J=11.0 Hz, 1H), 3.26 (t, J=1.9 Hz, 3H), 3.52 (br, 1H), 3.84 (d, J=1.7 Hz, 3H), 3.92 (s, 1H), 4.00 (d, J=4.1 Hz, 2H), 6.88 (m, 2H), 7.94 (m, 2H).

後処理

  1. concentrationthe mixture was concentrated in vacuo
  2. additionThe residue was diluted by the addition of CH2Cl2 and 1 N NaOH
  3. extractionextracted with CH2Cl2
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over Na2SO4, which
  6. concentrationwas concentrated in vacuo
  7. customThe residue was chromatographed on silica gel [50 g, CHCl3/MeOH (20/1)]

出典と根拠

ORDレコード
ord-f0cc63a0258d415c99db2e0d17bb5028
出典データセット
uspto-grants-2007_02
特許番号
US07179819B2

反応ノート

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