Berberine chloride → Dihydroberberine

HRID 1930097Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1930097
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][N+:7]3[CH2:20][CH2:19][C:18]4[C:13](=[CH:14][C:15]5[O:23][CH2:22][O:21][C:16]=5[CH:17]=4)[C:8]=3[CH:9]=2)[C:4]=1[O:24][CH3:25].[Cl-].[BH4-].[Na+].C(Cl)Cl.C(OCC)(=O)C.CO>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[CH:9]=[C:8]3[N:7]([CH2:20][CH2:19][C:18]4[CH:17]=[C:16]5[O:21][CH2:22][O:23][C:15]5=[CH:14][C:13]=43)[CH2:6][C:5]=2[C:4]=1[O:24][CH3:25]

Komponenten

5

Edukt 3

HCID 12456Berberine chlorideHCID 4311764Sodium borohydride2×HCID 21901258Dichloromethane ethyl acetate methanol

Produkt 1

HCID 10217DihydroberberineAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a solution of berberine hydrochloride (3,718 g, 10 mmol) in pyridine (30 mL) was added portionwise sodium borohydride (450 mg, 12 mmol) and the mixture was stirred at room temperature for 30 min. More sodium borohydride (380 mg, 10 mmol) was added and stirring was continued for 1 h. The reduction was monitored by TLC (DCM-ethyl acetate-methanol 4:4:2). The mixture was poured onto ice water. The precipitate was filtered, the residue washed with water and then dried under vacuum over calcium chloride to give 2.860 g of title compound in about 85 % yield.

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for 1 h
  3. additionThe mixture was poured onto ice water
  4. filtrationThe precipitate was filtered
  5. washthe residue washed with water
  6. dry with materialdried under vacuum over calcium chloride

Quellen und Nachweise

ORD-Eintrag
ord-3a9fd2ebc1234ff5bd9ebd61bee4665f
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188109B2

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