N,N,N',N'-Tetramethylethylenediamine → HCID 19902089, compound

HRID 2352419Notes

Reaction equation

HRID 2352419 reaction equation
C([Li])CCC.[F:6][C:7]1[CH:8]=[C:9]([CH:16]=[CH:17][CH:18]=1)[CH2:10]N1C=CN=C1.C[N:20]([CH3:26])[CH2:21][CH2:22][N:23](C)C.[CH:27]12[CH2:36][CH:31]3[CH2:32][CH:33]([CH2:35][CH:29]([CH2:30]3)[C:28]1=[O:37])[CH2:34]2>CCCCCC.O1CCCC1.O>[F:6][C:7]1[CH:8]=[C:9]([CH:10]([C:28]2([OH:37])[CH:29]3[CH2:35][CH:33]4[CH2:32][CH:31]([CH2:36][CH:27]2[CH2:34]4)[CH2:30]3)[C:26]2[NH:23][CH:22]=[CH:21][N:20]=2)[CH:16]=[CH:17][CH:18]=1

Participants

8

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 64151AdamantanoneHCID 199020871-[(3-Fluorophenyl)methyl]-1H-imidazoleHCID 178418339Butyllithium

Product 1

HCID 19902089HCID 19902089, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

55 ml (85 mmol) of a 1.55 molar solution of n-butyllithium in hexane were added dropwise to a solution of 7.04 g (40 mmol) of N-(3-fluorobenzyl)-imidazole and 4.65 g (40 mmol) of N,N,N',N'-tetramethylethylenediamine (TMEDA) in 90 ml of absolute tetrahydrofuran (THF) at -70° C. The mixture was stirred for a further 20 minutes at -70° C., and a solution of 6.01 g (40 mmol) of adamantanone in 30 ml of absolute tetrahydrofuran (THF) was then added dropwise at -70° C. in the course of about 15 minutes. Stirring was then continued for 15 minutes at about -70° C., the reaction mixture was allowed to warm up to room temperature in the course of about 2 hours, 200 ml of water were added at about 5°-18° C., while cooling, and the mixtures was extracted with CH2CL2. The combined CH2Cl2 extracts were dried, filtered, and evaporated down in vacuo. The residue of the extract was dissolved in acetonitrile, after which crystalline 3-fluorophenyl-(2-hydroxy-2-adamantyl)-imidazolylmethane was precipitated in pure form. After the crystalline product had been filtered off under suction and washed thoroughly with acetonitrile, 8.70 g of pure product of melting point 191° C. were obtained.

Workup

  1. stirringStirring
  2. waitwas then continued for 15 minutes at about -70° C.
  3. additionwere added at about 5°-18° C.
  4. temperaturewhile cooling
  5. extractionthe mixtures was extracted with CH2CL2
  6. dry with materialThe combined CH2Cl2 extracts were dried
  7. filtrationfiltered
  8. customevaporated down in vacuo
  9. dissolutionThe residue of the extract was dissolved in acetonitrile
  10. customafter which crystalline 3-fluorophenyl-(2-hydroxy-2-adamantyl)-imidazolylmethane was precipitated in pure form
  11. filtrationAfter the crystalline product had been filtered off under suction
  12. washwashed thoroughly with acetonitrile, 8.70 g of pure product of melting point 191° C.
  13. customwere obtained

Sources & evidence

ORD record
ord-74e3d415f21643628e8aed5d070f81c9
Source dataset
uspto-grants-1989_10
Patent number
US04876354

Reaction notes

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