HCID 3107899, compound → HCID 23355090, compound

HRID 234654Notes

Reaction equation

HRID 234654 reaction equation
[CH3:1][Li].[C:3]12([C:13](=[O:22])[CH:14]=[CH:15][C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2>C1COCC1.CCOCC>[C:3]12([C:13](=[O:22])[CH2:14][CH:15]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)[CH3:1])[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2

Participants

5

Reactant 2

HCID 3107899HCID 3107899, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 23355090HCID 23355090, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-18 °C

Procedure

To a suspension of cuprous bromide-dimethylsulfide (1.28 g, 6.25 mmol) in THF (20 ml) cooled to -18° C., was added dropwise methyllithium (1.4 M; 8.93 ml, 12.5 mmol) in ether. The resulting clear solution was left to stir for a further 45 minutes before a solution of 1-(1-adamantyl)-3-(3-pyridyl)-2-propen-1-one (1.34 g, 5.0 mmol) in THF (8 ml) was added at -18° C. After 4 hours at 0° C. the reaction mixture was quenched with aqueous ammonium hydroxide solution and extracted with ether. The ether extracts were combined, dried (Na2CO3) and concentrated. Chromatography, on elution with petrol-ether-triethylamine 125:50:1, provided the title compound (1.16 g, 82%) as an oil. Analytical data were the same as given in Example 10.

Workup

  1. waitThe resulting clear solution was left
  2. additionwas added at -18° C
  3. customAfter 4 hours at 0° C. the reaction mixture was quenched with aqueous ammonium hydroxide solution
  4. extractionextracted with ether
  5. dry with materialdried (Na2CO3)
  6. concentrationconcentrated
  7. washChromatography, on elution with petrol-ether-triethylamine 125:50:1

Sources & evidence

ORD record
ord-d07272c919f241b38d592042ec6e31d4
Source dataset
uspto-grants-1997_01
Patent number
US05595995

Reaction notes

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