HCID 54201797, compound → HCID 58081142, compound

HRID 2361752Notes

Reaction equation

HRID 2361752 reaction equation
[CH3:1][Mg]Br.[Br:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH:14]1[CH2:19][CH2:18][C:17](=[O:20])[CH2:16][CH2:15]1)[CH:9]=[CH:8]2>C1COCC1>[Br:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH:14]1[CH2:15][CH2:16][C:17]([CH3:1])([OH:20])[CH2:18][CH2:19]1)[CH:9]=[CH:8]2

Participants

4

Reactant 2

HCID 54201797HCID 54201797, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 58081142HCID 58081142, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methylmagnesium bromide (1.4 M solution in toluene/THF) (3.667 ml, 5.134 mmol) was added dropwise to a cooled solution (at 0° C.) of intermediate D30 (0.5 g, 1.711 mmol) in THF (20 ml) under a N2 atmosphere. The resulting reaction mixture was warmed to room temperature and further stirred for 4 h. After cooling in an ice bath, the mixture was carefully quenched with NH4Cl (aqueous sat. solution), and was subsequently extracted with DCM. The organic layer was separated, dried (Na2SO4), and the solvent was evaporated in vacuo. The crude residue was purified by column chromatography (silica gel; 0-30% EtOAc/heptane as eluent). The desired fractions were collected and the solvent was evaporated in vacuo to yield cis-D33 (0.096 g, 18.2%) and trans-D33 (0.12 g, 22.7%).

Workup

  1. customThe resulting reaction mixture
  2. temperatureAfter cooling in an ice bath
  3. customthe mixture was carefully quenched with NH4Cl (aqueous sat. solution)
  4. extractionwas subsequently extracted with DCM
  5. customThe organic layer was separated
  6. dry with materialdried (Na2SO4)
  7. customthe solvent was evaporated in vacuo
  8. customThe crude residue was purified by column chromatography (silica gel; 0-30% EtOAc/heptane as eluent)
  9. customThe desired fractions were collected
  10. customthe solvent was evaporated in vacuo
  11. customto yield cis-D33 (0.096 g, 18.2%) and trans-D33 (0.12 g, 22.7%)

Sources & evidence

ORD record
ord-95ee183b20af4508a7df47ef2b1569e7
Source dataset
uspto-grants-2014_04
Patent number
US08691813B2

Reaction notes

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