Toluene → (R)-ethyl-3-(4-chlorophenyl)-4-(2-propenyl)hexahydro-1-pyrazinecarboxylate

HRID 2390917노트

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HRID 2390917 반응식
Cl.Cl.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]2[CH2:15][N:14](CC3C=CC=CC=3)[CH2:13][CH2:12][N:11]2[CH2:23][CH:24]=[CH2:25])=[CH:6][CH:5]=1.C1(C)C=CC=CC=1.[OH-].[Na+].[C:35](Cl)(=[O:39])[O:36][CH2:37][CH3:38]>O.CCCCCC>[CH2:37]([O:36][C:35]([N:14]1[CH2:13][CH2:12][N:11]([CH2:23][CH:24]=[CH2:25])[C@H:10]([C:7]2[CH:6]=[CH:5][C:4]([Cl:3])=[CH:9][CH:8]=2)[CH2:15]1)=[O:39])[CH3:38]

참가 물질

7

반응물 4

HCID 1140TolueneHCID 10928Ethyl chloroformate2회HCID 14798Sodium HydroxideHCID 68577180(R)-2-(4-chlorophenyl)-4-(phenylmethyl)-1-(2-propenyl)hexahydropyrazine dihydrochloride

생성물 1

HCID 68576864(R)-ethyl-3-(4-chlorophenyl)-4-(2-propenyl)hexahydro-1-pyrazinecarboxylate수율 7.3%

시약·촉매·용매 2

HCID 962Water용매HCID 8058Hexane용매

반응 조건

온도
25 °C

실험 절차

In distilled water (5 mL), (R)-2-(4-Chlorophenyl)-4-(phenylmethyl)-1-(2-propenyl)hexahydropyrazine dihydrochloride (400 mg, 1.0 mmol) produced in Example 18 was dissolved. To the solution, toluene (5 mL) and 30 wt % aqueous solution of sodium hydroxide (401 mg, 3.0 equivalents) were added. After the organic layer and aqueous layer were separated, the organic layer was washed twice with distilled water (5 mL) and then concentrated. To the concentrate, hexane (5 mL) and ethyl chlorocarbonate (163 mg, 1.5 equivalents) were added. The mixture was stirred at 25° C. for 24 hours. Further, ethyl chlorocarbonate (328 mg, 3.0 equivalents) was added, and the mixture was stirred at 40° C. for 24 hours. After the mixture was cooled to 5° C., the precipitated crystals were collected by filtration under reduced pressure, washed with hexane (2 mL), and dried under vacuum, to obtain 22.5 mg of the title compound as while crystals (yield: 7%, chemical purity: 92.5 area %). Further, the filtrate was concentrated. To the concentrate, toluene (5 mL) was added and the toluene was distilled away. The operation was repeated 3 times. The obtained concentrate was dried under vacuum, to obtain 212 mg of the title compound as while turbid oil (yield: 69%, chemical purity: 95.9 area %). The retention time in the chemical purity analysis method was 22.7 min.

후처리

  1. customAfter the organic layer and aqueous layer were separated
  2. washthe organic layer was washed twice with distilled water (5 mL)
  3. concentrationconcentrated
  4. stirringthe mixture was stirred at 40° C. for 24 hours
  5. temperatureAfter the mixture was cooled to 5° C.
  6. filtrationthe precipitated crystals were collected by filtration under reduced pressure
  7. washwashed with hexane (2 mL)
  8. customdried under vacuum

출처 및 근거

ORD 기록
ord-96404e936c2c43fa91bada6eedf8b1f5
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08273883B2

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