Sodium Hydroxide → (R)-3-(4-chlorophenyl)-1-(phenylmethyl)hexahydropyrazine dihydrochloride

HRID 2390919노트

반응식

HRID 2390919 반응식
[ClH:1].Cl.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]2[CH2:15][N:14]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:13][CH2:12][N:11]2CC=C)=[CH:6][CH:5]=1.[OH-].[Na+]>[Ru](Cl)(Cl)Cl.C1(C)C=CC=CC=1>[ClH:3].[ClH:1].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C@H:10]2[NH:11][CH2:12][CH2:13][N:14]([CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:15]2)=[CH:8][CH:9]=1

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 68577180(R)-2-(4-chlorophenyl)-4-(phenylmethyl)-1-(2-propenyl)hexahydropyrazine dihydrochloride

생성물 1

HCID 68578904(R)-3-(4-chlorophenyl)-1-(phenylmethyl)hexahydropyrazine dihydrochloride수율 87%

시약·촉매·용매 2

HCID 61850Ruthenium trichloride촉매HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

Mixed were (R)-2-(4-Chlorophenyl)-4-(phenylmethyl)-1-(2-propenyl)hexahydropyrazine dihydrochloride (104 mg, 0.25 mmol) produced in Example 18 and ruthenium chloride (3 mg, 0.04 mmol). The mixture was stirred at 100° C. for 24 hours. To the mixture, 30 wt % aqueous solution of sodium hydroxide (85 mg, 2.5 equivalents) and toluene (2 mL) were added. The formed insolubles were separated by filtration, and washed with distilled water (2 mL) and toluene (2 mL). After the organic layer and aqueous layer of the filtrate were separated, the organic layer was washed twice with distilled water (4 mL). The obtained organic layer was concentrated and dried under vacuum, to obtain 68 mg of the crude product of the title compound as pale brown oil (yield: 87%, chemical purity: 93.5 area %, optical purity: 98.1% e.e.). The retention time in the chemical purity analysis method was 3.1 min.

후처리

  1. additionMixed
  2. customThe formed insolubles were separated by filtration
  3. washwashed with distilled water (2 mL) and toluene (2 mL)
  4. customAfter the organic layer and aqueous layer of the filtrate were separated
  5. washthe organic layer was washed twice with distilled water (4 mL)
  6. concentrationThe obtained organic layer was concentrated
  7. customdried under vacuum

출처 및 근거

ORD 기록
ord-6b48065f8e2b4c9cb5da246eaee62ab6
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08273883B2

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