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

HRID 2372801ノート

反応式

HRID 2372801 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 21883165Tetrahydrofuran hexane溶媒

反応条件

温度
-60 °C

実験手順

A solution of 4.05 g (20 mmol) of 2-(3-methyl-1-adamant-yl)-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.

後処理

  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

出典と根拠

ORDレコード
ord-e2e57341111244e1bf045d51c7da6d98
出典データセット
uspto-grants-1992_03
特許番号
US05100890

反応ノート

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