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 57989Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 57989
[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

Komponenten

4

Edukt 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

Produkt 1

HCID 86707174Tert-butyl 4-hydroxy-3-[6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]piperidine-1-carboxylateAusbeute 45,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-3a4ff994947e48afa24b7ae829c7738c
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434725B2

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