Trifluoroacetic acid → dimethyl (S)-4-(2-pyrrolidinylmethoxy)isophthalate

HRID 354302ノート

反応式

HRID 354302 の反応式
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][C:16]=1[C:25]([O:27][CH3:28])=[O:26])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][C:16]=1[C:25]([O:27][CH3:28])=[O:26]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 86595076dimethyl (S)-4-[1-(tert-butoxycarbonyl)-2-pyrrolidinylmethoxy]isophthalate

生成物 1

HCID 86595072dimethyl (S)-4-(2-pyrrolidinylmethoxy)isophthalate収率 53.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of dimethyl (S)-4-[1-(tert-butoxycarbonyl)-2-pyrrolidinylmethoxy]isophthalate (2.01 g, 5.11 mmol), TFA (20 mL), and CH2Cl2 (25 mL) was stirred for 1.5 hr at room temp. The resulting mixture was concentrated in vacuo and made basic with sat. NaHCO3. The mixture was extracted with CH2Cl2, washed with brine, dried over Na2CO3, and evaporated. The residue was purified by column chromatography on silica-gel with CHCl3—MeOH (9:1, v/v) as eluent to give 0.80 g (53%) dimethyl (S)4-(2-pyrrolidinylmethoxy)isophthalate as a yellow oil. 1H-NMR (CDCl3) δ1.71 (m, 1 H), 1.89 (m, 2 H), 2.00 (m, 1 H), 3.05-3.13 (m, 2 H), 3.67 (m, 1 H), 3.90 (s, 3 H), 3.91 (s, 3 H), 4.05-4.18 (m, 2H), 7.00 (d, 1 H, J=8.8 Hz), 8.14 (dd, 1 H, J=2.4, 8.8 Hz), 8.50 (d, 1 H, J=2.4 Hz).

後処理

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. extractionThe mixture was extracted with CH2Cl2
  3. washwashed with brine
  4. dry with materialdried over Na2CO3
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica-gel with CHCl3—MeOH (9:1

出典と根拠

ORDレコード
ord-b92632aa88fa4a8593452c90b5d6b614
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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