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Ammonium Chloride → Tert-butyl 3-[1-(3,5-difluorophenyl)-1-hydroxy-2,2-dimethylpropyl]azetidine-1-carboxylate

HRID 602702
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인쇄 미리보기

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HRID 602702 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)([CH3:25])([CH3:24])[CH3:23].[NH4+].[Cl-]>C1COCC1>[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:22]([CH3:25])([CH3:24])[CH3:23])[CH:18]=[C:19]([F:21])[CH:20]=1
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참가 물질

5

반응물 3

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

생성물 1

HCID 67065877Tert-butyl 3-[1-(3,5-difluorophenyl)-1-hydroxy-2,2-dimethylpropyl]azetidine-1-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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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-06e5cc734c194ddf838c98867f1648cd
출처 데이터셋
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07906503B2

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