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Ethyl Acetate → (R)-tert-butyl 3-(6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)piperidine-1-carboxylate

HRID 1969739
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HRID 1969739 반응식
S([N:11]1[C:15]2[N:16]=[CH:17][C:18]3[N:19]([C:20]([C@@H:23]4[CH2:28][CH2:27][CH2:26][N:25]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:24]4)=[N:21][CH:22]=3)[C:14]=2[CH:13]=[CH:12]1)(C1C=CC(C)=CC=1)(=O)=O.[OH-].[Na+].CCOC(C)=O.[NH4+].[Cl-]>O1CCOCC1>[C:20]1([C@@H:23]2[CH2:28][CH2:27][CH2:26][N:25]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:24]2)[N:19]2[C:14]3[CH:13]=[CH:12][NH:11][C:15]=3[N:16]=[CH:17][C:18]2=[CH:22][N:21]=1
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참가 물질

6

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HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 58557605(R)-tert-butyl 3-(6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)piperidine-1-carboxylate

생성물 1

HCID 58557937(R)-tert-butyl 3-(6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)piperidine-1-carboxylate수율 92%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
60 °C

실험 절차

To a solution of (R)-tert-butyl 3-(6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)piperidine-1-carboxylate (4.44 g, 8.96 mmol) in 1,4-dioxane (54 mL) was added NaOH (2 N aqueous, 8.9 mL, 18 mmol), and the resulting mixture was heated at about 60° C. for about 3 h. The reaction was cooled to ambient temperature and EtOAc (30 mL) and saturated aqueous NH4Cl (20 mL) were added. The organic layer was separated and the aqueous layer was further extracted with EtOAc (40 mL). The combined organic layers were washed with brine (40 mL), dried over anhydrous MgSO4, filtered, and concd under reduced pressure. The material was purified by silica gel chromatography eluting with a gradient of 0-10% MeOH in DCM to afford (R)-tert-butyl 3-(6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)piperidine-1-carboxylate (2.80 g, 92%): LC/MS (Table 1, Method b) Rt=1.85 min; MS m/z: 342 (M+H)+.

후처리

  1. temperatureThe reaction was cooled to ambient temperature
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was further extracted with EtOAc (40 mL)
  4. washThe combined organic layers were washed with brine (40 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. customThe material was purified by silica gel chromatography
  8. washeluting with a gradient of 0-10% MeOH in DCM

출처 및 근거

ORD 기록
ord-7c5b762c0f2c4c1a8534e197fe360e45
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08426411B2

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