Reaktion #1090360

ord-69a0be22a0734d9ebc507790a65dad55

Reaktionsgleichung

C[C@]12CC[C@@H]3c4ccc(OCc5ccccc5)cc4CC[C@H]3[C@@H]1CCC2=O
3-benzyloxyestra-1,3,5(10)-trien-17-one
C[C@]12CC[C@@H]3c4ccc(OCc5ccccc5)cc4CC[C@H]3[C@@H]1CCC2=O
3-Benzyloxyestra-1,3,5(10)-trien-17-one
[BH4-].[Na+]
sodium borohydride
→
C[C@]12CC[C@@H]3c4ccc(OCc5ccccc5)cc4CC[C@H]3[C@@H]1CC[C@@H]2O
41
Ausbeute 100.4%
C[C@]12CC[C@@H]3c4ccc(OCc5ccccc5)cc4CC[C@H]3[C@@H]1CC[C@@H]2O
3-Benzyloxyestra-1,3,5(10)-trien-17β-ol
Ausbeute 100.4%

Edukte

C[C@]12CC[C@@H]3c4ccc(OCc5ccccc5)cc4CC[C@H]3[C@@H]1CCC2=O
3-benzyloxyestra-1,3,5(10)-trien-17-one
C[C@]12CC[C@@H]3c4ccc(OCc5ccccc5)cc4CC[C@H]3[C@@H]1CCC2=O
3-Benzyloxyestra-1,3,5(10)-trien-17-one
[BH4-].[Na+]
sodium borohydride

Reagenzien

Keine

Lösungsmittel

C1CCOC1
THF
CO
MeOH

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigequenched with saturated aqueous NH4Cl, and H2O
  2. 2
    workup.ADDITIONadded
  3. 3
    FiltrationThe precipitate was collected by filtration
  4. 4
    Waschenwashed with H2O

Vorschrift

To a solution of 3-benzyloxyestra-1,3,5(10)-trien-17-one (40, 2.70 g, 7.5 mmol) in THF (5.0 mL) and MeOH (30 mL) was added sodium borohydride (284 mg, 7.5 mmol) at 0° C. The reaction mixture was stirred for 30 min, then quenched with saturated aqueous NH4Cl, and H2O added. The precipitate was collected by filtration and washed with H2O to afford 2.73 g of 41 (100% yield) mp: 118-119° C.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06046186uspto-grants-2000_04