HCID 22846511, compound → HCID 22846512, compound

HRID 2254869Notes

Reaction equation

HRID 2254869 reaction equation
[CH3:1][N:2]1[C:19](=[O:20])[CH2:18][CH2:17][C@@:16]2([CH3:21])[C:3]1=[CH:4][CH:5]([CH3:23])[C@@H:6]1[C@@H:15]2[CH2:14][CH2:13][C@@:11]2([CH3:12])[C@H:7]1[CH2:8][CH2:9][CH:10]2[OH:22]>C(O)(=O)C.[Pt](=O)=O>[CH3:1][N:2]1[C:19](=[O:20])[CH2:18][CH2:17][C@@:16]2([CH3:21])[CH:3]1[CH2:4][CH:5]([CH3:23])[C@@H:6]1[C@@H:15]2[CH2:14][CH2:13][C@@:11]2([CH3:12])[C@H:7]1[CH2:8][CH2:9][CH:10]2[OH:22]

Participants

4

Reactant 1

HCID 22846511HCID 22846511, compound

Product 1

HCID 22846512HCID 22846512, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 11 from Example 10, being 350 mg in 10 ml acetic acid was added 100 mg catalytic platinum dioxide and the resulting mixture was evacuated and flushed with hydrogen. The reaction was shaken overnight at room temperature under 40 Psig hydrogen pressure. The solution was filtered and concentrated to a residue. The residue was worked up with ethyl acetate, the organic layer was then concentrated under vacuum, diluted with ethyl acetate, washed with aqueous NaHCO3, brine, dried, concentrated to yield the title compound 12. Mass Spec: 320, (M+1).

Workup

  1. customthe resulting mixture was evacuated
  2. customflushed with hydrogen
  3. filtrationThe solution was filtered
  4. concentrationconcentrated to a residue
  5. concentrationthe organic layer was then concentrated under vacuum
  6. additiondiluted with ethyl acetate
  7. washwashed with aqueous NaHCO3, brine
  8. customdried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-45361e05c79149a1a81c28456cb4901e
Source dataset
uspto-grants-1993_08
Patent number
US05237064

Reaction notes

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