Sodium borohydride → HCID 588676、化合物

HRID 361605ノート

反応式

HRID 361605 の反応式
[C:1]1([C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]=1.[BH4-].[Na+]>CO.O>[CH:1]1([C:11]2[CH:12]=[CH:13][C:14]([C:15]#[N:16])=[CH:17][CH:18]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1

参加物

5

反応物 2

HCID 4311764Sodium borohydrideHCID 539726084-(3,4-Dihydroisoquinolin-1-yl)benzonitrile

生成物 1

HCID 588676HCID 588676、化合物収率 89.7%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒2 回

実験手順

A solution of 3.48 g of 4-(3,4-dihydro-isoquinolin-1-yl)-benzonitrile in 90 ml of methanol was cooled to 5° C. while stirring and treated with 1.7 g of sodium borohydride within 30 min. After completion of the addition, the mixture was stirred at 5° C. for a further 30 min. Subsequently, 50 ml of water were slowly added dropwise and the mixture was stirred at room temperature for a further 10 min. The mixture was diluted with water and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and evaporated. 3.15 g of crystalline (RS)-4-(1,2,3,4-tetrahydro-isoquinolin-1-yl)-benzonitrile were obtained. Recrystallization of a sample from diisopropyl ether gave colorless crystals of m.p. 94°-97° C.

後処理

  1. additionAfter completion of the addition
  2. stirringthe mixture was stirred at 5° C. for a further 30 min
  3. stirringthe mixture was stirred at room temperature for a further 10 min
  4. extractionextracted three times with ethyl acetate
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. customevaporated

出典と根拠

ORDレコード
ord-bc55606960c04fbaa56f3c902fdc940f
出典データセット
uspto-grants-1999_02
特許番号
US05866583

反応ノート

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