Dimethylformamide → HCID 54256830, compound

HRID 1780516Notes

Reaction equation

HRID 1780516 reaction equation
[CH3:1][N:2]1[C@H:11]2[C@@:6]([CH3:24])([C:7]3[CH:15]=[CH:14][C:13]([CH:16]=[CH:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:12][C:8]=3[CH2:9][CH2:10]2)[CH2:5][CH2:4][C:3]1=[O:25].CN(C)C=O>C(O)C.[Pd]>[CH3:1][N:2]1[C@H:11]2[C@@:6]([CH3:24])([C:7]3[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:12][C:8]=3[CH2:9][CH2:10]2)[CH2:5][CH2:4][C:3]1=[O:25]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 54514540HCID 54514540, compound

Product 1

HCID 54256830HCID 54256830, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A 150 mg portion of the product of Example 279 was hydrogenated on a Parr apparatus at 40 p.s.i. in 50 mL of ethanol containing 5 mL of dimethylformamide and 20 mg of 10% palladium/carbon catalyst. When the starting material had been consumed, the mixture was filtered and the filtrate was concentrated under vacuum. The residue was purified by chromatography on silica gel, eluting with 90% ethyl acetate/hexane to obtain a product which was recrystallized from ethyl acetate/hexane to produce the desired product. m.p. 109°-111°.

Workup

  1. customWhen the starting material had been consumed
  2. filtrationthe mixture was filtered
  3. concentrationthe filtrate was concentrated under vacuum
  4. customThe residue was purified by chromatography on silica gel
  5. washeluting with 90% ethyl acetate/hexane
  6. customto obtain a product which
  7. customwas recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-77d2961479044a5f88a3b9652fe35297
Source dataset
uspto-grants-1997_05
Patent number
US05629007

Reaction notes

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