HCID 67159582, compound → HCID 67159662, compound

HRID 1255184Notes

Reaction equation

HRID 1255184 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8]([C:11]3[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH3:21])[CH:12]=3)=[CH:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[H][H]>CCOC(C)=O.[Pt](=O)=O>[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH3:21])[CH:12]=3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 67159582HCID 67159582, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67159662HCID 67159662, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a degassed solution of the title compound from Example 13 Step B (606 mg, 2.10 mmol) in EtOAc (15 mL) was added platinum(IV) oxide (150 mg). The reaction mixture was fitted with a 3-way adapter with a hydrogen balloon attached. The reaction flask was then evacuated and back-filled with hydrogen. After this process was repeated three times, the reaction mixture was placed under a hydrogen atmosphere, then was stirred vigorously. After 45 min, the reaction mixture was filtered through Celite, rinsing with EtOAc. The mixture was then concentrated in vacuo to provide the title compound, which was used without further purification: LCMS m/z 259.4 [M−CH3O]+.

Workup

  1. customThe reaction flask was then evacuated
  2. additionback-filled with hydrogen
  3. filtrationthe reaction mixture was filtered through Celite
  4. washrinsing with EtOAc
  5. concentrationThe mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-20c82665b96040e7ba9219a4650fa97b
Source dataset
uspto-grants-2013_06
Patent number
US08455638B2

Reaction notes

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