Reaction #1747895

ord-818618f2fe9741ea83ffd94b6c26a69c

Reaction equation

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

Reactants

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

Reagents

None

Solvents

C1CCOC1
THF

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherquenched with 10 ml of saturated aqueous NH4Cl and 50 ml of H2O
  2. 2
    workup.ADDITIONadded
  3. 3
    FiltrationThe precipitate was collected by filtration
  4. 4
    Washwashed with H2O

Procedure

To a suspension of 3-benzyloxyestra-1,3,5(10)-trien-17-one BLE99049 (3.46 g, 9.59 mmol) in THF (15 ml) and MeOH (38 ml) was added sodium borohydride (0.36 g, 9.58 mmol) at 0° C. The reaction mixture was stirred for 30 min at room temperature, then quenched with 10 ml of saturated aqueous NH4Cl and 50 ml of H2O added. The precipitate was collected by filtration and washed with H2O to afford 3.50 g of 3-benzyloxyestra-1,3,5(10)-trien-17β-ol BLE99051 (100% crude yield) as a white solid.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08030296B2uspto-grants-2011_10