HCID 19754904, compound → HCID 19754868, compound

HRID 1588906Notes

Reaction equation

HRID 1588906 reaction equation
[CH:1]1([N:6]([CH:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)[C:7](=[O:26])[C:8]2[CH:13]=[CH:12][C:11]([CH:14]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=3)O)=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>C(O)C.S(=O)(=O)(O)O.[Pd].C(OCC)(=O)C.CCCCCC>[CH:27]1([N:6]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[C:7](=[O:26])[C:8]2[CH:9]=[CH:10][C:11]([CH2:14][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=3)=[CH:12][CH:13]=2)[CH2:28][CH2:29][CH2:30][CH2:31]1

Participants

7

Reactant 1

HCID 19754904HCID 19754904, compound

Product 1

HCID 19754868HCID 19754868, compound

Reagents, catalysts & solvents 5

HCID 1118Sulfuric AcidCatalystHCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound prepared in Example 10 (0.40 g, 0.84 mmol) in ethyl alcohol (20 mL) containing concentrated sulfuric acid (2 drops) was hydrogenated at 60 psi and room temperature using 5% Pd/C as catalyst. The catalyst was filtered and the filtrate concentrated in vacuo to give the crude product as an oil. Chromatography of the crude product on silica gel using mixtures of ethyl acetate and hexane as eluents gave the title compound as a crystalline solid, m. pt. 138-142° C.

Workup

  1. customwas hydrogenated at 60 psi and room temperature
  2. filtrationThe catalyst was filtered
  3. concentrationthe filtrate concentrated in vacuo
  4. customto give the crude product as an oil

Sources & evidence

ORD record
ord-da935a48a7f64d9c901a61887bf570c7
Source dataset
uspto-grants-1993_06
Patent number
US05223539

Reaction notes

Loading…