Ammonium Chloride → HCID 59331940、化合物

HRID 924767ノート

反応式

HRID 924767 の反応式
[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]

参加物

4

反応物 3

HCID 25517Ammonium ChlorideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 178505943HCID 178505943、化合物

生成物 1

HCID 59331940HCID 59331940、化合物収率 30.4%

実験手順

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).

後処理

  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%)

出典と根拠

ORDレコード
ord-d59c09399af947d0b145610d004559ac
出典データセット
uspto-grants-2016_03
特許番号
US09283226B2

反応ノート

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