Water → 5-(Pent-4-enyl)-2,3-diphenyl-5,6,7,8-tetrahydropyrido[3,2-b]pyrazine

HRID 406208

반응식

HRID 406208 반응식
[C:1]1([C:7]2[N:12]=[C:11]3[CH2:13][CH2:14][CH2:15][NH:16][C:10]3=[N:9][C:8]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:23](=O)[CH2:24][CH2:25][CH:26]=[CH2:27].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>ClCCCl>[CH2:27]([N:16]1[C:10]2[C:11](=[N:12][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[C:8]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:9]=2)[CH2:13][CH2:14][CH2:15]1)[CH2:26][CH2:25][CH:24]=[CH2:23]

참가 물질

6

반응물 4

HCID 962WaterHCID 164184-PentenalHCID 5049666Sodium triacetoxyborohydrideHCID 666655612,3-Diphenyl-5,6,7,8-tetrahydropyrido[3,2-b]pyrazine

생성물 1

HCID 666663485-(Pent-4-enyl)-2,3-diphenyl-5,6,7,8-tetrahydropyrido[3,2-b]pyrazine

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

To a solution of 2,3-diphenyl-5,6,7,8-tetrahydropyrido[3,2-b]pyrazine (Ex. 4.1 step 1) (2 g, 6.96 mmol) in DCE (35 ml) was added pent-4-enal (2.061 ml, 20.88 mmol) and the mixture was stirred at RT overnight. A further portion of sodium triacetoxyborohydride (4.43 g, 20.88 mmol) was added and the mixture was stirred at RT for 2.5 hours under an atmosphere of nitrogen. Water was added and the mixture was extracted with EtOAc (3×60 ml). The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo. The crude material was purified by chromatography on silica eluting with EtOAc/iso-hexane to afford the title compound;

후처리

  1. stirringthe mixture was stirred at RT for 2.5 hours under an atmosphere of nitrogen
  2. extractionthe mixture was extracted with EtOAc (3×60 ml)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by chromatography on silica eluting with EtOAc/iso-hexane

출처 및 근거

ORD 기록
ord-ba3f6fb4214f4382b6814a3ccf8c095f
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08754085B2

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