Hydrochloric Acid → 2-Butyl-8-hydroxy-3-oxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile

HRID 416590ノート

反応式

HRID 416590 の反応式
[CH2:1]([N:5]1[C:14](=[O:15])[C:13]([C:16]#[N:17])=[C:12]2[C:7]([C:8](=[O:18])[CH2:9][CH2:10][CH2:11]2)=[CH:6]1)[CH2:2][CH2:3][CH3:4].[BH4-].[Na+].Cl>C1COCC1>[CH2:1]([N:5]1[C:14](=[O:15])[C:13]([C:16]#[N:17])=[C:12]2[C:7]([CH:8]([OH:18])[CH2:9][CH2:10][CH2:11]2)=[CH:6]1)[CH2:2][CH2:3][CH3:4]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 222664802-Butyl-3,8-dioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile

生成物 1

HCID 222665102-Butyl-8-hydroxy-3-oxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile収率 75.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

2-Butyl-3,8-dioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile (7-011) (10 mg, 0.04 mmol) was dissolved in THF (1 mL), and to the reaction mixture was added sodium borohydride (2.1 mg, 0.056 mmol), and the reaction mixture was stirred at room temperature for 10 min. To the reaction mixture was added diluted hydrochloric acid (1 mol/L, 3 mL), and the reaction mixture was extracted with ethyl acetate (10 mL), washed with brine (5 mL), dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The obtained crystalloid residue was recrystallized from methylene chloride to give 2-butyl-8-hydroxy-3-oxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile (7-013) (7.4 mg, 75%) as a white crystal.

後処理

  1. extractionthe reaction mixture was extracted with ethyl acetate (10 mL)
  2. washwashed with brine (5 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe obtained crystalloid residue was recrystallized from methylene chloride

出典と根拠

ORDレコード
ord-12d0a4e075c548509d82868d53d7f4eb
出典データセット
uspto-grants-2012_01
特許番号
US08088924B2

反応ノート

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