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

HRID 1493744노트

반응식

HRID 1493744 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 21883165Tetrahydrofuran hexane용매

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온도
-60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2a17c32cf2024be9808de8b143a2f413
출처 데이터셋
uspto-grants-1991_06
특허 번호
US05023357

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