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

HRID 354289노트

반응식

HRID 354289 반응식
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:16]=[C:17]([C:25]([O:27][CH3:28])=[O:26])[C:18](=[CH:23][CH:24]=1)[C:19]([O:21][CH3:22])=[O:20])=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:16]=[C:17]([C:25]([O:27][CH3:28])=[O:26])[C:18](=[CH:23][CH:24]=1)[C:19]([O:21][CH3:22])=[O:20]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 86587781dimethyl (S)-4-[1-(tert-butoxycarbonyl)-2-pyrrolidinylmethoxy]phthalate

생성물 1

HCID 86595075dimethyl (S)-4-(2-pyrrolidinylmethoxy)phthalate수율 18.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of dimethyl (S)-4-[1-(tert-butoxycarbonyl)-2-pyrrolidinylmethoxy]phthalate (5.75 g, 14.62 mmol) in CH2Cl2 (25 mL) was added TFA (20 mL), and the resulting mixture was stirred for 50 min at room temp. The resulting mixture was concentrated in vacuo and made basic with sat. NaHCO3. The mix was extracted with CH2Cl2, washed with brine, dried over MgSO4, and evaporated off in vacuo. The residue was purified by column chromatography on silica-gel with CHCl3—MeOH (50:1, v/v) as eluent to give 790 mg (18%) dimethyl (S)-4-(2-pyrrolidinylmethoxy)phthalate as a brown oil. 1H-NMR (CDCl3) δ1.48-1.57 (m, 1 H), 1.72-1.84 (m, 2 H), 1.89-1.98 (m, 2 H), 2.91-3.03 (m, 2 H), 3.48-3.54 (m, 1 H), 3.82-3.97 (m, total 8 H), 6.98 (dd, 1 H, J=2.4, 8.8 Hz), 7.06 (d, 1 H, J=2.4 Hz), 7.78 (d, 1 H, J=8.8 Hz).

후처리

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. extractionThe mix was extracted with CH2Cl2
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated off in vacuo
  6. customThe residue was purified by column chromatography on silica-gel with CHCl3—MeOH (50:1

출처 및 근거

ORD 기록
ord-162e2812dd894409922269ef404d9bac
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06756378B2

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