Sodium borohydride → Ethyl 9-methyl-6-oxo-6,7,8,9-tetrahydropyrido[3',2':4,5]pyrrolo[1,2-a]pyrazine-2-carboxylate

HRID 1521719ノート

反応式

HRID 1521719 の反応式
[C:1]([CH:3]([N:5]1[C:9]2=[N:10][C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][CH:13]=[C:8]2[CH:7]=[C:6]1[C:19]([O:21]CC)=O)[CH3:4])#[N:2].[BH4-].[Na+]>CO.C1COCC1>[CH3:4][CH:3]1[N:5]2[C:9]3[N:10]=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:12]=[CH:13][C:8]=3[CH:7]=[C:6]2[C:19](=[O:21])[NH:2][CH2:1]1

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 67236322Diethyl 1-(1-cyanoethyl)-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate

生成物 1

HCID 67239191Ethyl 9-methyl-6-oxo-6,7,8,9-tetrahydropyrido[3',2':4,5]pyrrolo[1,2-a]pyrazine-2-carboxylate収率 43%

試薬・触媒・溶媒 1

HCID 21899815MeOH tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

To a solution of diethyl 1-(1-cyanoethyl)-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate (807 mg, 2.56 mmol) in methanol/THF (14 mL, 1:1 v/v) at 0° C. is added sodium borohydride (968 mg, 25.6 mmol). The cold bath is removed and the reaction mixture is stirred for 30 min, at which point the reaction vessel is sealed and warmed to 60° C. After being stirred for 4 h, the mixture is cooled to room temperature and diluted with EtOAc. The organic phase is washed twice with 1Ma aqueous NaHSO4 and once with brine, is dried (Na2SO4), filtered and concentrated to provide the title compound as a light yellow solid (298 mg, 43%).

後処理

  1. customThe cold bath is removed
  2. customis sealed
  3. stirringAfter being stirred for 4 h
  4. temperaturethe mixture is cooled to room temperature
  5. additiondiluted with EtOAc
  6. washThe organic phase is washed twice with 1Ma aqueous NaHSO4 and once with brine
  7. dry with materialis dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-7e952f4712b245a2bfa26928a3fa76cd
出典データセット
uspto-grants-2015_07
特許番号
US09073926B2

反応ノート

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