Reaktion #220370

ord-dd37dfd8276044ac8aeefb8ec0f2bc04

Reaktionsgleichung

Cc1ccc2[nH]c3c(cc(-c4cccc(C=O)c4)c(=O)n3C)c2c1
compound
Cc1ccc2[nH]c3c(cc(-c4cccc(C=O)c4)c(=O)n3C)c2c1
3-(1,6-Dimethyl-2-oxo-2,9-dihydro-1H-pyrido[2,3-b]-indol-3-yl)benzaldehyde
CC(=O)O
AcOH
CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]
NaBH(OAc)3
→
Cc1ccc2[nH]c3c(cc(-c4cccc(CO)c4)c(=O)n3C)c2c1
expected compound
Ausbeute 71.0%
Cc1ccc2[nH]c3c(cc(-c4cccc(CO)c4)c(=O)n3C)c2c1
3-(3-Hydroxymethylphenyl)-1,6-dimethyl-1,9-dihydro-2H-pyrido[2,3-b]indol-2-one
Ausbeute 71.0%

Edukte

Cc1ccc2[nH]c3c(cc(-c4cccc(C=O)c4)c(=O)n3C)c2c1
compound
Cc1ccc2[nH]c3c(cc(-c4cccc(C=O)c4)c(=O)n3C)c2c1
3-(1,6-Dimethyl-2-oxo-2,9-dihydro-1H-pyrido[2,3-b]-indol-3-yl)benzaldehyde
CC(=O)O
AcOH
CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]
NaBH(OAc)3

Reagenzien

Keine

Lösungsmittel

ClCCl
CH2Cl2

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONare added
  2. 2
    workup.WAITthe mixture is left
  3. 3
    SonstigeThe reaction medium is evaporated
  4. 4
    Filtrationfiltration

Vorschrift

280 mg of the compound obtained in Stage A are placed in 10 ml of CH2Cl2 and the minimum amount of AcOH to dissolve the compound, 375 mg of NaBH(OAc)3 are added and then the mixture is left stirring at AT for 18 hours. The reaction medium is evaporated and the residue is taken up in AcOEt and then filtration is carried out to produce 200 mg of the expected compound.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07390818B2uspto-grants-2008_06