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 57989ノート

反応式

HRID 57989 の反応式
[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

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-3a4ff994947e48afa24b7ae829c7738c
出典データセット
uspto-grants-2016_09
特許番号
US09434725B2

反応ノート

読み込み中…