Water → 2-(3-Chlorophenyl)-2-(1-imidazolyl)-1-(3-methyladamant-1-ylmethyl)-ethanol

HRID 1493744Notes

Reaction equation

HRID 1493744 reaction equation
[CH3:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][C:4]([CH2:12][CH:13]=[O:14])([CH2:5]3)[CH2:3]1)[CH2:9]2.[Li].[Cl:16][C:17]1[CH:18]=[C:19]([CH:26]=[CH:27][CH:28]=1)[CH2:20][N:21]1[CH:25]=[CH:24][N:23]=[CH:22]1.O>C1COCC1.C1COCC1.CCCCCC>[Cl:16][C:17]1[CH:18]=[C:19]([CH:20]([N:21]2[CH:25]=[CH:24][N:23]=[CH:22]2)[CH:13]([CH2:12][C:4]23[CH2:5][CH:6]4[CH2:7][CH:8]([CH2:9][C:2]([CH3:1])([CH2:11]4)[CH2:3]2)[CH2:10]3)[OH:14])[CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 962WaterHCID 199020902-(3-Methyl-1-adamantyl)-acetaldehydeHCID 67919603lithium N-(3-chlorobenzyl)-imidazole

Product 1

HCID 199020842-(3-Chlorophenyl)-2-(1-imidazolyl)-1-(3-methyladamant-1-ylmethyl)-ethanolYield 24.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21883165Tetrahydrofuran hexaneSolvent

Conditions

Temperature
-60 °C

Procedure

A solution of 4.05 g (20 mmol) of 2-(3-methyl-1-adamantyl)-acetaldehyde (95% pure) in 40 ml of absolute THF was added, at about -60° C., to a solution of 20 mmol of lithium-N-(3-chlorobenzyl)-imidazole in THF/hexane, the said solution being prepared analogously to Example 105, and the mixture was stirred for 45 minutes at about -60° C. and for 1.75 hours at -60° C. to room temperature. After about 200 ml of water had been added, the mixture was extracted with ether. The residue (8.8 g) from the ether extract was crystallized from diisopropyl ether, and the product obtained was then recrystallized from acetonitrile. After isolation, 1.90 g (=24.7% of theory) of 2-(3-chlorophenyl)-2-(1-imidazolyl)-1-(3-methyladamant-1-ylmethyl)-ethanol of melting point 126° C. were obtained as a diastereomer which was pure according to thin layer chromatography. According to thin layer chromatography, the mother liquor contained further amounts of the same diastereomer, and the other diastereomer as the principal component.

Workup

  1. customthe said solution being prepared analogously to Example 105
  2. extractionthe mixture was extracted with ether
  3. extractionThe residue (8.8 g) from the ether extract
  4. customwas crystallized from diisopropyl ether
  5. customthe product obtained
  6. customwas then recrystallized from acetonitrile

Sources & evidence

ORD record
ord-2a17c32cf2024be9808de8b143a2f413
Source dataset
uspto-grants-1991_06
Patent number
US05023357

Reaction notes

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