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

HRID 1483958노트

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HRID 1483958 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

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+).

후처리

  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%)

출처 및 근거

ORD 기록
ord-3016610f3aad473e82f03a5d26e3df95
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09420814B2

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