Reaction #1543040

ord-60917a74a962497696e42c7766135847

Reaction equation

C[C@]12CC[C@H](O)C[C@H]1CC[C@@H]1[C@@H]2C[C@@H](O)[C@]2(C)[C@@H](C3=CC(=O)OC3)CC[C@]12O
Digoxigenin
O=O
oxygen
→
C[C@]12[C@H](O)CC3C(CC[C@@H]4CC(=O)CC[C@]34C)[C@@]1(O)CC[C@@H]2C1=CC(=O)OC1
white solid
Yield 101.5%
C[C@]12[C@H](O)CC3C(CC[C@@H]4CC(=O)CC[C@]34C)[C@@]1(O)CC[C@@H]2C1=CC(=O)OC1
3-Ketodigoxigenin
Yield 101.5%

Reactants

C[C@]12CC[C@H](O)C[C@H]1CC[C@@H]1[C@@H]2C[C@@H](O)[C@]2(C)[C@@H](C3=CC(=O)OC3)CC[C@]12O
Digoxigenin
O=O
oxygen

Reagents

[Pt]
Platinum

Solvents

CC(C)=O
acetone
O
water

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Filtrationwas filtered off

Procedure

Platinum IV oxide (0.5 g) was added to 1.0 g of Digoxigenin and dissolved in 100 mls of water and 150 mls of acetone. The mixture was pressurized to 2 atmospheres of oxygen and shaken for catalyst was filtered off, and the solvent stripped off leaving 1.01 g of white solid. This was dissolved in 100 mls of methylene chloride and extracted with 70 mls of water. The water was back-washed with two volumes of 50 mls of methylene chloride. The organic fractions were collected, dried with anhydrous sodium sulfate and the solvent was stripped off leaving 0.75 g of white solid.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05843634uspto-grants-1998_12