Acetic Acid → (2S,4S)-4-acetoxy-1-tert-butoxycarbonyl-2-pyrrolidinemethanol

HRID 354425노트

반응식

HRID 354425 반응식
[C:1]([O:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:7]([CH2:17][O:18][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:6]1)(=[O:3])[CH3:2].C(O)(=O)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:1]([O:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])[C@H:7]([CH2:17][OH:18])[CH2:6]1)(=[O:3])[CH3:2]

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 69340895(2S,4S)4-acetoxy-1-tert-butoxycarbonyl-2-tert-butyldiphenylsilyloxymethypyrrolidine

생성물 1

HCID 69332993(2S,4S)-4-acetoxy-1-tert-butoxycarbonyl-2-pyrrolidinemethanol수율 79.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred mixture of (2S,4S)-4-acetoxy-1-tert-butoxycarbonyl-2-tert-butyldiphenylsilyloxymethypyrrolidine (23.3 g, 46.9 mmol) and acetic acid (6.0 ml, 104.8 mmol) in THF (470 ml) was added TBAF (93.8 ml, 93.8 mmol) at 0° C. After 24 h stirring, the mixture was concentrated in vacuo. The resulting residue was diluted with EtOAC and aq. NH4Cl and extracted with EtOAc. The combined extracts were washed with brine, which were dried over Na2SO4 and concntrated in vacuo. The residue was chromatographed on silica gel (700 g, CHCl3/EtOAc (4/1)], to give (2S,4S)-4-acetoxy-1-tert-butoxycarbonyl-2-pyrrolidinemethanol (9.70 g, 8%) as a colorless oil. 1H-NMR (CDCl3) δ1.47 (s, 9H), 1.63 (m, 1H), 1.81 (m, 1H), 2.07 (s, 3H), 234 (m, 1H), 3.42 (dd, J=12.7, 0.9 Hz, 1H), 3.62-3.85 (m, 3H), 4.48 (br, 1H), 5.20 (br, 1H).

후처리

  1. concentrationthe mixture was concentrated in vacuo
  2. additionThe resulting residue was diluted with EtOAC and aq. NH4Cl
  3. extractionextracted with EtOAc
  4. washThe combined extracts were washed with brine, which
  5. dry with materialwere dried over Na2SO4
  6. customThe residue was chromatographed on silica gel (700 g, CHCl3/EtOAc (4/1)],

출처 및 근거

ORD 기록
ord-f0c6640ccda3407f99f24e9b6f48e8c5
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06756378B2

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