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

HRID 354302노트

반응식

HRID 354302 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b92632aa88fa4a8593452c90b5d6b614
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06756378B2

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