Trifluoroacetic acid → methyl 4-[5-(R)-phenyl-2-(S)-pirrolidinylmethoxy]benzate

HRID 350502노트

반응식

HRID 350502 반응식
C([N:8]1[C@@H:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:11][CH2:10][C@H:9]1[CH2:19][O:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=1)(OC(C)(C)C)=O.FC(F)(F)C(O)=O>C(Cl)Cl>[C:13]1([C@@H:12]2[NH:8][C@H:9]([CH2:19][O:20][C:21]3[CH:22]=[CH:23][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:29][CH:30]=3)[CH2:10][CH2:11]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 20737850HCID 20737850, 화합물

생성물 1

HCID 69332954methyl 4-[5-(R)-phenyl-2-(S)-pirrolidinylmethoxy]benzate수율 37.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of methyl 4-[N-Boc-5-(R)-phenyl-2-(S)-pyrrolidinylmethoxy]benzoate (1.28 g, 3.11 mmol) in CH2Cl2 (30 ml) was added trifluoroacetic acid (10 ml) at rt, and the resulting mixture was stirred for 45 min. The mixture was concentrated in vacuo and poured into aq.NaHCO3, then extracted with CHCl3. The organic layer was washed with water, drying over anhydrous Na2SO4, and concentrated in vacuo to give methyl 4-[5-(R)-phenyl-2-(S)-pirrolidinyl methoxy]benzate (363 mg, quant.) as yellowish oil. The product was used for next reactions without further purification. 1H-NMR (CDCl3) δ 1.71–1.83 (m, 2 H), 2.03–2.10 (m, 1 H), 2.15–2.24 (m, 1 H), 3.68–3.74 (m, 1 H), 3.89 (s, 3 H), 4.01–4.09 (m, 2 H), 4.28 (t, J=7.2 Hz, 1 H), 6.95 (d, J=8.8 Hz, 2 H), 7.22–7.27 (m, 1 H), 7.33 (t, J=8.0 Hz, 2 H), 7.42 (d, J=7.6 Hz, 2 H), 8.00 (d, J=8.8 Hz, 2 H); MS (ESI) m/z, 312 (M++H) 353 (M++CH3CN).

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. additionpoured into aq
  3. extractionNaHCO3, then extracted with CHCl3
  4. washThe organic layer was washed with water
  5. dry with materialdrying over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-7e948042a5024a7a8010f62d3145310f
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179819B2

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