Sodium borohydride → 10-Hydroxy-4-methoxy-1'-methyl-9,10-dihydroanthracene-9-spiro-4'-piperidine

HRID 1576271Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1576271
[CH3:1][O:2][C:3]1[C:8]2[C:9](=[O:23])[C:10]3[C:15]([C:16]4([CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]4)[C:7]=2[CH:6]=[CH:5][CH:4]=1)=[CH:14][CH:13]=[CH:12][CH:11]=3.[BH4-].[Na+]>C(O)C.O>[OH:23][CH:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:16]2([CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]2)[C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]1=2

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 867339644-Methoxy-1'-methyl-10-oxo-9,10-dihydroanthracene-9-spiro-4'-piperidine

Produkt 1

HCID 8673396310-Hydroxy-4-methoxy-1'-methyl-9,10-dihydroanthracene-9-spiro-4'-piperidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

4-Methoxy-1'-methyl-10-oxo-9,10-dihydroanthracene-9-spiro-4'-piperidine (1.8 g.), in ethanol (100 ml.) is treated with sodium borohydride (2 g.), allowed to stand at room temperature overnight, then the reaction mixture is diluted with water and extracted with ether. The ether is washed with water, dried (MgSO4) and evaporated to give an oil which is chromatographed on magnesium silicate. Elution with toluene-ethyl acetate gives 10-hydroxy-4-methoxy-1'-methyl-9,10-dihydroanthracene-9-spiro-4'-piperidine, m.p. 149°-151°C. on recrystallisation from aqueous ethanol.

Aufarbeitung

  1. extractionextracted with ether
  2. washThe ether is washed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give an oil which
  6. customis chromatographed on magnesium silicate
  7. washElution with toluene-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-6a6a68e9d53a454b9e38ae89110353d4
Quelldatensatz
uspto-grants-1976_09
Patentnummer
US03979513

Notizen zur Reaktion

Wird geladen…