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

HRID 350492노트

반응식

HRID 350492 반응식
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

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 16093620HCID 16093620, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)]

출처 및 근거

ORD 기록
ord-f0cc63a0258d415c99db2e0d17bb5028
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179819B2

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