Tetrahydrofuran → 2-Amino-5-(benzyloxy)-2-(difluoromethyl)pentanenitrile

HRID 1995576

반응식

HRID 1995576 반응식
Cl[CH2:2][CH2:3][CH2:4][O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Mg:13].[F:14][CH:15]([F:18])[C:16]#[N:17].C1COCC1.[C-:24]#[N:25].[Na+].[Cl-:27].[NH4+]>CCOCC.O>[CH2:6]([O:5][CH2:4][CH2:3][CH2:2][Mg:13][Cl:27])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[F:14][CH:15]([F:18])[C:16]([NH2:17])([CH2:2][CH2:3][CH2:4][O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:24]#[N:25]

참가 물질

10

반응물 6

HCID 8028TetrahydrofuranHCID 8929Sodium CyanideHCID 25517Ammonium ChlorideHCID 120219Acetonitrile, difluoro-HCID 221505((3-Chloropropoxy)methyl)benzeneHCID 5462224Magnesium

생성물 2

HCID 204820032-Amino-5-(benzyloxy)-2-(difluoromethyl)pentanenitrileHCID 178479006HCID 178479006, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 3283Diethyl Ether용매

반응 조건

온도
-40 °C

실험 절차

Under an atmosphere of nitrogen, 3-benzyloxypropyl-magnesium chloride is prepared from 1-chloro-3-benzyloxypropane (2.42 g, 13 mmol) in dry ether (13 ml) and magnesium turnings (660 mg, 26 mmol). The Grignard solution is separated from the excess of magnesium, cooled to -40° C., and a 10% solution of difluoroacetonitrile in dry THF (10 ml, 13 mmol) is added dropwise, maintaining the temperature at -40° C. After stirring at this temperature, for 30 minutes, the mixture is poured into a cold (0° C.) solution of sodium cyanide (1.27 g) and ammonium chloride (2.10 g) in water (40 ml). The mixture is stirred vigorously for 1 hour; during that time the reaction is allowed to warm up to room temperature. The organic phase is separated and extracted with 2 N HCl. Basification with concentrated ammonia (pH ~9-10), extraction with ether, drying, and evaporation gives the title compound as an oil (1.5 g).

후처리

  1. customThe Grignard solution is separated from the excess of magnesium
  2. temperaturemaintaining the temperature at -40° C
  3. stirringThe mixture is stirred vigorously for 1 hour
  4. temperatureto warm up to room temperature
  5. customThe organic phase is separated
  6. extractionextracted with 2 N HCl
  7. extractionBasification with concentrated ammonia (pH ~9-10), extraction with ether
  8. customdrying
  9. customevaporation

출처 및 근거

ORD 기록
ord-cf812cdd388f40c282d2623d4a68ff30
출처 데이터셋
uspto-grants-1983_09
특허 번호
US04405530

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