HCID 54073594, compound → HCID 131715823, compound

HRID 330524Notes

Reaction equation

HRID 330524 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:30]=[CH:31][C:32]=1[O:33][CH3:34])[CH2:6][NH:7][CH:8]([CH2:17]NCC1C=CC(OC)=C(OC)C=1)[CH:9]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[OH:10]>C(O)C.O=[Pt]=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:30]=[CH:31][C:32]=1[O:33][CH3:34])[CH2:6][NH:7][C:8]([NH:7][CH2:6][C:5]1[CH:30]=[CH:31][C:32]([O:33][CH3:34])=[C:3]([O:2][CH3:1])[CH:4]=1)([CH3:17])[CH:9]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[OH:10]

Participants

4

Reactant 1

HCID 54073594HCID 54073594, compound

Product 1

HCID 131715823HCID 131715823, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A solution of 83 g of (5) in 200 ml of absolute ethanol, containing 0.3 g of PtO2 was hydrogenated at atmospheric pressure and room temperature. After 24 hours, the catalyst was filtered off and the solvent evaporated. The crude product was chromatographed on a silica gel column with EtOAc-Et3N-MeOH (90:5:5) to give diamine (6) (41.5 g) with a 47.6% yield from (4).

Workup

  1. customwas hydrogenated at atmospheric pressure and room temperature
  2. filtrationthe catalyst was filtered off
  3. customthe solvent evaporated
  4. customThe crude product was chromatographed on a silica gel column with EtOAc-Et3N-MeOH (90:5:5)

Sources & evidence

ORD record
ord-24eb544688c24456b403b4995eb8b629
Source dataset
uspto-grants-1990_01
Patent number
US04897412

Reaction notes

Loading…