Hydrochloric Acid → 3(S)-(3,4-dichlorophenyl)-4-(imidazol-1-yl)butan-1-ol

HRID 844585ノート

反応式

HRID 844585 の反応式
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([C@@H:11]([CH2:15][N:16]2[CH:20]=[CH:19][N:18]=[CH:17]2)[CH2:12][CH:13]=[O:14])[CH:7]=[CH:8][C:9]=1[Cl:10].Cl.[OH-].[Na+]>C(O)C.O>[Cl:3][C:4]1[CH:5]=[C:6]([C@@H:11]([CH2:15][N:16]2[CH:20]=[CH:19][N:18]=[CH:17]2)[CH2:12][CH2:13][OH:14])[CH:7]=[CH:8][C:9]=1[Cl:10]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 544333793(S)-(3,4-dichlorophenyl)-4-(imidazol-1-yl)butan-1-al

生成物 1

HCID 541546783(S)-(3,4-dichlorophenyl)-4-(imidazol-1-yl)butan-1-ol収率 31.6%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

Sodium borohydride (0.68 g) was added carefully to an ice-cooled solution of 3(S)-(3,4-dichlorophenyl)-4-(imidazol-1-yl)butan-1-al (4.3 g) (see Preparation 97) in ethanol (40 ml) and the mixture stirred at room temperature for one hour before removing the solvent under reduced pressure to give a residue. The residue was suspended in water (30 ml), cooled in an ice-bath and the mixture first acidified to pH1 with 2N aqueous hydrochloric acid solution and then basified to pH14 by addition of 2N aqueous sodium hydroxide solution. The resulting suspension was filtered and the residue washed with water, dried and then crystallised from acetonitrile to give 3(S)-(3,4-dichlorophenyl)-4-(imidazol-1-yl)butan-1-ol (1.37 g) as a cream solid.

後処理

  1. custombefore removing the solvent under reduced pressure
  2. customto give a residue
  3. temperaturecooled in an ice-bath
  4. filtrationThe resulting suspension was filtered
  5. washthe residue washed with water
  6. customdried
  7. customcrystallised from acetonitrile

出典と根拠

ORDレコード
ord-a010e5f5fc674100a9ca214937a2bd5a
出典データセット
uspto-grants-2002_04
特許番号
US06380396B1

反応ノート

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