Sodium cyanoborohydride → [2-(3-Fluoro-4-nitro-phenyl)-ethyl]-dimethyl-amine

HRID 58171

반응식

HRID 58171 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][N:13]([CH3:15])[CH3:14])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[BH3-]C#N.[Na+]>CO.CC(O)=O>[F:1][C:2]1[CH:3]=[C:4]([CH2:11][CH2:12][N:13]([CH3:14])[CH3:15])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

참가 물질

5

반응물 2

HCID 5003444Sodium cyanoborohydrideHCID 91252016[2-(3-Fluoro-4-nitro-phenyl)-vinyl]-dimethyl-amine

생성물 1

HCID 118024700[2-(3-Fluoro-4-nitro-phenyl)-ethyl]-dimethyl-amine수율 63.6%

시약·촉매·용매 2

HCID 176Acetic Acid촉매HCID 887Methanol용매

실험 절차

To a solution of [2-(3-fluoro-4-nitro-phenyl)-vinyl]-dimethyl-amine (1.7 g, 8 mmol) in MeOH, was added NaBH3CN (770 g, 12 mmol) and one drop of AcOH. The reaction mixture was stirred at room temperature for 2 hours and quenched with water. After removal of all volatiles in vacuo, the residue was extracted with 10% methanol in DCM twice. The combined extracts were washed with brine, dried over anhydrous sodium sulfate. Concentration under vacuum gave a crude product, which was purified by reverse phase column to afford the title compound (1.08 g, yield: 63%). MS (ESI): 213 [M+H]+

후처리

  1. customquenched with water
  2. customAfter removal of all volatiles in vacuo
  3. extractionthe residue was extracted with 10% methanol in DCM twice
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationConcentration under vacuum
  7. customgave a crude product, which
  8. customwas purified by reverse phase column

출처 및 근거

ORD 기록
ord-c800bd55957a40af80233547b65c2632
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434697B2

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