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

HRID 844585Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 844585
[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]

Komponenten

7

Edukt 4

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

Produkt 1

HCID 541546783(S)-(3,4-dichlorophenyl)-4-(imidazol-1-yl)butan-1-olAusbeute 31,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a010e5f5fc674100a9ca214937a2bd5a
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06380396B1

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