HCID 22875679, compound → HCID 22875680, compound

HRID 2258008Notes

Reaction equation

HRID 2258008 reaction equation
[Si:1]([O:8][CH:9]([C@@H:11]1[C@:28]2([CH3:29])[C@H:14]([C@H:15]3[C@H:25]([CH2:26][CH2:27]2)[C@:23]2([CH3:24])[C:18]([NH:19][CH2:20][CH2:21][CH2:22]2)=[CH:17][C@@H:16]3[CH3:30])[CH2:13][CH2:12]1)[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C(O)(=O)C.[Pt]=O>[Si:1]([O:8][CH:9]([C@@H:11]1[C@:28]2([CH3:29])[C@H:14]([C@H:15]3[C@H:25]([CH2:26][CH2:27]2)[C@:23]2([CH3:24])[C@H:18]([NH:19][CH2:20][CH2:21][CH2:22]2)[CH2:17][C@@H:16]3[CH3:30])[CH2:13][CH2:12]1)[CH3:10])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 22875679HCID 22875679, compound

Product 1

HCID 22875680HCID 22875680, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 20-tert-butyldimethylsilyloxy-7β-methyl-4-azapregn-5-ene (23.9 gms, 53.6 mmol) in acetic acid (250 mL) was added platinum oxide (1.8 gm). The mixture was stirred overnight under hydrogen (1 atmosphere). The reaction mixture was filtered through a pad of celite filter aid and the filtrate was coevaporated with toluene (3×500 mL) to remove all of the acetic acid. The residue was dissolved in chloroform and filtered again through a pad of celite filter aid to remove residual catalyst. The solvent was removed by rotoevaporation to yield the title compound which was taken directly on to the next step without any further purification.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. filtrationfilter aid
  3. customto remove all of the acetic acid
  4. dissolutionThe residue was dissolved in chloroform
  5. filtrationfiltered again through a pad of celite
  6. filtrationfilter aid
  7. customto remove residual catalyst
  8. customThe solvent was removed by rotoevaporation

Sources & evidence

ORD record
ord-01e6cd6e58634d8b853d72ef9821ddd4
Source dataset
uspto-grants-1997_08
Patent number
US05658922

Reaction notes

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