N,N,N',N'-Tetramethylethylenediamine → HCID 67919629, compound

HRID 2352424Notes

Reaction equation

HRID 2352424 reaction equation
C([Li])CCC.CCCCCC.[CH3:12][C:13]1[CH:14]=[C:15]([CH:22]=[CH:23][CH:24]=1)[CH2:16]N1C=CN=C1.C[N:26]([CH2:28][CH2:29][N:30]([CH3:32])C)C.[CH:33]12[CH2:42][CH:37]3[CH2:38][CH:39]([CH2:41][CH:35]([CH2:36]3)[C:34]1=[O:43])[CH2:40]2>C1COCC1.O>[OH:43][C:34]1([CH:16]([C:15]2[CH:14]=[C:13]([CH3:12])[CH:24]=[CH:23][CH:22]=2)[C:32]2[NH:30][CH:29]=[CH:28][N:26]=2)[CH:33]2[CH2:42][CH:37]3[CH2:38][CH:39]([CH2:41][CH:35]1[CH2:36]3)[CH2:40]2

Participants

7

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 64151AdamantanoneHCID 18679298HCID 18679298, compoundHCID 178418244HCID 178418244, compound

Product 1

HCID 67919629HCID 67919629, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-70 °C

Procedure

39 ml (60.5 mmol) of 1,55 molar n-butyllithium/hexane solution were added dropwise to a solution of 5.17 g (30 mmol) of N-(3-methylbenzyl)-imidazole and 3.49 g (30 mmol) of TMEDA in 60 ml of absolute THF at -70° C. The mixture was stirred for 30 minutes at -70° C., after which a solution of 4.51 g of adamantanone in 35 ml of absolute tetrahydrofuran was added dropwise at about -70° C., stirring was continued for 20 minutes at -70° C., the mixture was allowed to warm up to room temperature, 300 ml of water were added, while cooling, and the mixture was then stirred for 15 minutes at about 5° C. Thereafter, the crystalline substance which had separated out was filtered off with suction, rinsed with water and hexane, dried and boiled up with about 25 ml of CH3CN for 3 minutes. After cooling, the solid was again filtered off under suction and dried. 3.87 g (=40% yield) of pure (2-hydroxy-2-adamantyl)-1-imidazolyl-(3-tolyl)-methane of melting point 186° C. were obtained.

Workup

  1. stirringstirring
  2. waitwas continued for 20 minutes at -70° C.
  3. temperatureto warm up to room temperature
  4. temperaturewhile cooling
  5. stirringthe mixture was then stirred for 15 minutes at about 5° C
  6. customThereafter, the crystalline substance which had separated out
  7. filtrationwas filtered off with suction
  8. washrinsed with water and hexane
  9. customdried
  10. waitboiled up with about 25 ml of CH3CN for 3 minutes
  11. temperatureAfter cooling
  12. filtrationthe solid was again filtered off under suction
  13. customdried

Sources & evidence

ORD record
ord-f76b7a8c893045e0927663f1753de1c0
Source dataset
uspto-grants-1989_10
Patent number
US04876354

Reaction notes

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