HCID 59780451, compound → HCID 68623264, compound

HRID 222555Notes

Reaction equation

HRID 222555 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]([CH2:18][C:19]([OH:21])=[O:20])=[CH:5]2.[H][H]>CO.[Ni]>[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH:6]([CH2:18][C:19]([OH:21])=[O:20])[CH2:5]2

Participants

5

Reactant 2

HCID 59780451HCID 59780451, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68623264HCID 68623264, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

1.00 g (3.61 mmol) of 13 was taken up in 80 ml of methanol, 1 g of Raney Ni (water-wet) was added, and the mixture was hydrogenated overnight at 50° C. at a hydrogen pressure of 5 bar. The catalyst was filtered off, the filtrate was evaporated to dryness, and the residue was purified by column chromatography (ethyl acetate/cyclohexane), giving a yellowish solid, which was identified as the racemic cis-compound 14.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated to dryness
  3. customthe residue was purified by column chromatography (ethyl acetate/cyclohexane)
  4. customgiving a yellowish solid, which

Sources & evidence

ORD record
ord-87450239fc2549afb1318f5938f8b622
Source dataset
uspto-grants-2012_06
Patent number
US08207345B2

Reaction notes

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