HCID 22875679, compound → HCID 22875680, compound

HRID 362799Notes

Reaction equation

HRID 362799 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, compound2×

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 g, 53.6 mmol, product of Step 8) 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 (trademark for diatomaceous earth) 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 roto-evaporation 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 (trademark for diatomaceous earth)
  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 roto-evaporation

Sources & evidence

ORD record
ord-1eedab24260746c5840d835b610c2253
Source dataset
uspto-grants-1999_02
Patent number
US05872126

Reaction notes

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