Hydrochloric Acid → (R)-ethyl-3-(4-chlorophenyl)-hexahydro-1-pyrazinecarboxylate

HRID 2390923노트

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HRID 2390923 반응식
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9](CC=C)[C@H:8]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH2:7]1)=[O:5])[CH3:2].O.Cl.[OH-].[Na+]>[Ru](Cl)(Cl)Cl.C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][NH:9][C@H:8]([C:15]2[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=2)[CH2:7]1)=[O:5])[CH3:2]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 68576864(R)-ethyl-3-(4-chlorophenyl)-4-(2-propenyl)hexahydro-1-pyrazinecarboxylate

생성물 1

HCID 68579181(R)-ethyl-3-(4-chlorophenyl)-hexahydro-1-pyrazinecarboxylate수율 38.8%

시약·촉매·용매 2

HCID 61850Ruthenium trichloride촉매HCID 1140Toluene용매

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온도
100 °C

실험 절차

To (R)-ethyl-3-(4-chlorophenyl)-4-(2-propenyl)hexahydro-1-pyrazinecarboxylate (212 mg, 0.69 mmol) produced in Example 24, distilled water (2 mL), conc. hydrochloric acid (71 mg, 1.0 equivalent) and ruthenium chloride (7 mg, 0.04 equivalent) were added. The mixture was stirred at 100° C. for 93 hours. After toluene (2 mL) was added thereto, the formed insolubles were separated by filtration and washed with toluene (2 mL) and distilled water (2 mL). To the filtrate, 30 wt % aqueous solution sodium hydroxide (110 mg, 1.2 equivalents) was added. The organic layer and aqueous layer were separated, and the organic layer was washed twice with distilled water (4 mL). The obtained organic layer was concentrated and dried under vacuum, to obtain 72 mg of the title compound as pale brown oil (yield: 38%, chemical purity: 92.6 area %). The retention time in the chemical purity analysis method was 2.9 min.

후처리

  1. additionwere added
  2. customthe formed insolubles were separated by filtration
  3. washwashed with toluene (2 mL)
  4. distillationdistilled water (2 mL)
  5. customThe organic layer and aqueous layer were separated
  6. washthe organic layer was washed twice with distilled water (4 mL)
  7. concentrationThe obtained organic layer was concentrated
  8. customdried under vacuum

출처 및 근거

ORD 기록
ord-8e7a6a6f0f2f4d91af0aa6c0b6df5c7c
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08273883B2

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