Triacetoxyperiodinane → 3,3-dimethyl-4-oxo-4-[5-triisopropylsilanyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-butyronitrile

HRID 1677524노트

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HRID 1677524 반응식
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][CH:24]([C:31]1[C:39]2[C:34](=[N:35][CH:36]=[C:37]([C:40]3[CH:45]=[C:44]([O:46][CH3:47])[C:43]([O:48][CH3:49])=[C:42]([O:50][CH3:51])[CH:41]=3)[N:38]=2)[N:33]([Si:52]([CH:59]([CH3:61])[CH3:60])([CH:56]([CH3:58])[CH3:57])[CH:53]([CH3:55])[CH3:54])[CH:32]=1)[C:25]([CH3:30])([CH3:29])[CH2:26][C:27]#[N:28]>ClCCl>[CH3:30][C:25]([CH3:29])([C:24](=[O:23])[C:31]1[C:39]2[C:34](=[N:35][CH:36]=[C:37]([C:40]3[CH:45]=[C:44]([O:46][CH3:47])[C:43]([O:48][CH3:49])=[C:42]([O:50][CH3:51])[CH:41]=3)[N:38]=2)[N:33]([Si:52]([CH:56]([CH3:58])[CH3:57])([CH:53]([CH3:54])[CH3:55])[CH:59]([CH3:61])[CH3:60])[CH:32]=1)[CH2:26][C:27]#[N:28]

참가 물질

4

반응물 2

HCID 159087TriacetoxyperiodinaneHCID 595407864-hydroxy-3,3-dimethyl-4-[5-triisopropylsilanyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-butyronitrile

생성물 1

HCID 595409513,3-dimethyl-4-oxo-4-[5-triisopropylsilanyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-butyronitrile수율 61.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
2.5 °C

실험 절차

Dess-Martin periodinane (0.122 g, 0.289 mmol) was added to a 0-5° C. solution of 4-hydroxy-3,3-dimethyl-4-[5-triisopropylsilanyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-butyronitrile (0.152 g, 0.275 mmol) in 2 mL of dichloromethane. The mixture was stirred at 0-5° C. for 3 h, then quenched with water and a sat. aq. NaHCO3 solution and extracted with 30 mL of dichloromethane. The organic layer was dried over MgSO4, filtered and concentrated to a residue. Column chromatography (0→50% EtOAc/hexanes) afforded 0.093 g (61%) of 3,3-dimethyl-4-oxo-4-[5-triisopropylsilanyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-butyronitrile as a white solid.

후처리

  1. customquenched with water
  2. extractiona sat. aq. NaHCO3 solution and extracted with 30 mL of dichloromethane
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to a residue

출처 및 근거

ORD 기록
ord-397cc17a29fe485090246bb036375ebc
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08008298B2

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