Triethylamine → (R)-2-((1-butyrylpiperidin-2-yl)methoxy)-6-nitrobenzonitrile

HRID 2280144ノート

反応式

HRID 2280144 の反応式
FC(F)(F)C([O-])=O.[C:8]([C:10]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][CH:21]=[CH:20][C:11]=1[O:12][CH2:13][C@H:14]1[CH2:19][CH2:18][CH2:17][CH2:16][NH2+:15]1)#[N:9].C(N(CC)CC)C.[C:34](Cl)(=[O:38])[CH2:35][CH2:36][CH3:37]>C(Cl)Cl>[C:34]([N:15]1[CH2:16][CH2:17][CH2:18][CH2:19][C@@H:14]1[CH2:13][O:12][C:11]1[CH:20]=[CH:21][CH:22]=[C:23]([N+:24]([O-:26])=[O:25])[C:10]=1[C:8]#[N:9])(=[O:38])[CH2:35][CH2:36][CH3:37]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 86714290(R)-2-((2-cyano-3-nitrophenoxy)methyl)piperidin-1-ium 2,2,2-trifluoroacetate

生成物 1

HCID 86714289(R)-2-((1-butyrylpiperidin-2-yl)methoxy)-6-nitrobenzonitrile収率 75.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a solution of (R)-2-((2-cyano-3-nitrophenoxy)methyl)piperidin-1-ium 2,2,2-trifluoroacetate (Example 16c, 2.26 g, 6.03 mmol) in anhydrous DCM (50 mL) was added triethylamine (4.2 mL, 30.1 mmol) at room temperature. The reaction mixture was cooled down to 0° C. and butyryl chloride (0.95 mL, 9.05 mmol) was added and the solution stirred at room temperature overnight. The solvent was then removed under reduced pressure and the residue was diluted with EtOAc (150 mL), the organic layer was washed successively with water, brine and dried over Na2SO4, filtered and evaporated. The residue was purified by Biotage SP-1 (40s column) eluting with EtOAc/Hexane (10%-70%) to give the desired product (1.5 g. 75%). MS 332 (MH+).

後処理

  1. customThe solvent was then removed under reduced pressure
  2. additionthe residue was diluted with EtOAc (150 mL)
  3. washthe organic layer was washed successively with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by Biotage SP-1 (40s column)
  8. washeluting with EtOAc/Hexane (10%-70%)

出典と根拠

ORDレコード
ord-3ddb4f2c44024e27b424c3f934738bb3
出典データセット
uspto-grants-2015_09
特許番号
US09138013B2

反応ノート

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