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Tetrahydrofuran → Tert-butyl 3-[1-(3,5-difluorophenyl)-1-hydroxy-2,2-diethylpropyl]azetidine-1-carboxylate

HRID 1724210
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HRID 1724210 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([F:21])[CH:20]=1)[C:5]([CH:7]1[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8]1)=[O:6].[C:22]([Mg]Cl)(C)(C)[CH3:23].[NH4+].[Cl-].[CH2:30]1[CH2:34]O[CH2:32][CH2:31]1>>[F:1][C:2]1[CH:3]=[C:4]([C:5]([CH:7]2[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])[CH2:8]2)([OH:6])[C:31]([CH2:22][CH3:23])([CH2:30][CH3:34])[CH3:32])[CH:18]=[C:19]([F:21])[CH:20]=1
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참가 물질

5

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HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 670659051,1-Dimethylethyl 3-(3,5-difluorobenzoyl)-1-azetidinecarboxylateHCID 178418310HCID 178418310, 화합물

생성물 1

HCID 69057678Tert-butyl 3-[1-(3,5-difluorophenyl)-1-hydroxy-2,2-diethylpropyl]azetidine-1-carboxylate

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온도
-78 °C

실험 절차

To a solution of 3.07 g (10.34 mmol) of tert-butyl 3-(3,5-difluorobenzoyl)azetidine-1-carboxylate in 20 mL of THF, 36.19 mL (36.19 mmol) of tert-butyl magnesium chloride was added and stirred for 3.5 h at −78° C. To the solution was added 8 mL of aq. NH4Cl and the solution was filtered to remove the solid. The filtrate was washed with ether. The combined organic layer was concentrated to remove solvents and residue was purified by silica gel chromatography with hexanes/ethyl acetate to afford the title compound; 1H-NMR(CDCl3) δ 0.897 (s, 9H), 1.425 (s, 9H), 2.234(br, 1H), 3.25 (m, 1H), 3.55 (m, 1H), 3.71 (t, J=8.9 Hz, 1H), 3.97 (t, J=8.4 Hz, 1H), 4.17(m ,1H), 6.53-6.74 (m, 3H).

후처리

  1. filtrationthe solution was filtered
  2. customto remove the solid
  3. washThe filtrate was washed with ether
  4. concentrationThe combined organic layer was concentrated
  5. customto remove solvents and residue
  6. customwas purified by silica gel chromatography with hexanes/ethyl acetate

출처 및 근거

ORD 기록
ord-bc3320d818bb4b5c9719c03e656f66c9
출처 데이터셋
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07485732B2

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