Ammonium Chloride → HCID 59331940, 화합물

HRID 924767노트

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HRID 924767 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][C:3]=1[F:10].[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][C:21](=[O:24])[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].[Cl-].[NH4+]>>[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][C:21]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([F:10])[CH:4]=2)([OH:24])[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

참가 물질

4

반응물 3

HCID 25517Ammonium ChlorideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 178505943HCID 178505943, 화합물

생성물 1

HCID 59331940HCID 59331940, 화합물수율 30.4%

실험 절차

A solution of 4-chloro-3-fluorophenylmagnesium bromide (15 ml, 7.5 mmol, 0.5M in THF) was added, under nitrogen, to 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (1.02 g, 5.1 mmol). After 24 hours, saturated ammonium chloride solution was added then the organic solvent was removed in vacuo. The mixture was extracted with ethyl acetate, then this extract was washed with brine, dried (MgSO4), filtered and concentrated to afford a residue which was purified by column chromatography (SiO2), eluting with gradient of ethyl acetate/petrol (0% to 20%) to afford the title compound (511 mg, 30%). 1H NMR (Me-d3-OD) δ 1.48 (9H, s), 1.67 (2H, br. d), 1.92 (2H, td), 3.16-3.29 (2H, m), 3.99 (2H, br. d), 7.27 (1H, dd), 7.38 (1H, dd), 7.42 (1H, t).

후처리

  1. customthe organic solvent was removed in vacuo
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthis extract was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford a residue which
  8. customwas purified by column chromatography (SiO2)
  9. washeluting with gradient of ethyl acetate/petrol (0% to 20%)

출처 및 근거

ORD 기록
ord-d59c09399af947d0b145610d004559ac
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09283226B2

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