Sodium borohydride → Tert-butyl 4-hydroxy-3-[6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]piperidine-1-carboxylate

HRID 57989노트

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HRID 57989 반응식
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[N:13]=[CH:12][C:11]3[CH:14]=[N:15][N:16]([C:17]4[N:22]=[C:21]([CH:23]5[C:28](=[O:29])[CH2:27][CH2:26][N:25]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:24]5)[CH:20]=[CH:19][CH:18]=4)[C:10]=3[CH:9]=2)[CH:5]=[N:4][CH:3]=1.[BH4-].[Na+]>O1CCCC1>[OH:29][CH:28]1[CH2:27][CH2:26][N:25]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:24][CH:23]1[C:21]1[CH:20]=[CH:19][CH:18]=[C:17]([N:16]2[C:10]3[CH:9]=[C:8]([C:6]4[CH:5]=[N:4][CH:3]=[C:2]([CH3:1])[N:7]=4)[N:13]=[CH:12][C:11]=3[CH:14]=[N:15]2)[N:22]=1

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 86707157Tert-butyl 3-[6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-4-oxo-piperidine-1-carboxylate

생성물 1

HCID 86707174Tert-butyl 4-hydroxy-3-[6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]piperidine-1-carboxylate수율 45.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a solution of tert-butyl 3-[6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-4-oxo-piperidine-1-carboxylate (90 mg, 0.18 mmol) in tetrahydrofuran (8.0 ml) at 0° C. was added sodium borohydride (8.0 mg, 0.20 mmol). The reaction mixture was stirred at 0° C. for 30 min. The reaction was quenched with water and extracted with EtOAc. The organic layers was dried with sodium sulfate, filtered, and concentrated in vacuum. The crude product was purified by flash chromatography (EtOAc/Heptane eluted at 100% EtOAc) to give the desired product 40 mg 44% yield. MS (ESI) m/z: 488.1.

후처리

  1. customThe reaction was quenched with water
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layers was dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum
  6. customThe crude product was purified by flash chromatography (EtOAc/Heptane eluted at 100% EtOAc)

출처 및 근거

ORD 기록
ord-3a4ff994947e48afa24b7ae829c7738c
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434725B2

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