2-Bromopropane → HCID 16063596, compound

HRID 1993935Notes

Reaction equation

HRID 1993935 reaction equation
[C:1]12([C:11]3[C:12](=[O:17])[NH:13][NH:14][C:15]=3[CH3:16])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.Br[CH:19]([CH3:21])[CH3:20]>CN(C=O)C>[C:1]12([N:13]3[C:12](=[O:17])[CH:20]=[C:19]([CH3:21])[N:14]3[CH:15]([CH3:16])[CH3:11])[CH2:2][CH:3]3[CH2:9][CH:7]([CH2:6][CH:5]([CH2:4]3)[CH2:10]1)[CH2:8]2.[C:1]12([C:11]3[C:12](=[O:17])[NH:13][N:14]([CH:19]([CH3:21])[CH3:20])[C:15]=3[CH3:16])[CH2:2][CH:3]3[CH2:9][CH:7]([CH2:6][CH:5]([CH2:4]3)[CH2:10]1)[CH2:8]2

Participants

5

Reactant 2

HCID 63582-BromopropaneHCID 13675783HCID 13675783, compound

Product 2

HCID 16063596HCID 16063596, compoundYield 34.5%HCID 68677971HCID 68677971, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A sealable tube was charged with 4-adamantan-1-yl-5-methyl-1,2-dihydro-pyrazol-3-one (0.05 g), 2-bromopropane (0.026 g) and DMF and purged with argon and sealed. The reaction vessel was immersed into a heated oil bath at 110 degrees C. for 48 hours. The reaction vessel was then cooled and opened carefully. The reaction mixture was diluted with EtOAc and aq. NaHCO3 solution and the phases were separated. The aqueous layer was extracted with further EtOAc and the combined organic layers were washed with sodium thiosulfate. The phases were then dried over sodium sulfate, filtered and reduced in vacuo. The crude gum was chromatographed by adsorption onto silica gel and subjection to Isco Combiflash chromatography. Evaporation of the desired fractions afforded the desired product 4-adamantan-1-yl-1-isopropyl-5-methyl-1,2-dihydro-pyrazol-3-one (0.01 g) as an off white material. MS (ESI+): 275.3 [M+H]+).

Workup

  1. custompurged with argon
  2. customsealed
  3. customThe reaction vessel was immersed into a heated oil bath at 110 degrees C
  4. temperatureThe reaction vessel was then cooled
  5. additionThe reaction mixture was diluted with EtOAc and aq. NaHCO3 solution
  6. customthe phases were separated
  7. extractionThe aqueous layer was extracted with further EtOAc
  8. washthe combined organic layers were washed with sodium thiosulfate
  9. dry with materialThe phases were then dried over sodium sulfate
  10. filtrationfiltered
  11. customThe crude gum was chromatographed by adsorption onto silica gel and subjection to Isco Combiflash chromatography
  12. customEvaporation of the desired fractions

Sources & evidence

ORD record
ord-2153feb7c0bd4c00b6e4e3134883c589
Source dataset
uspto-grants-2010_01
Patent number
US07652057B2

Reaction notes

Loading…