Water → Cyclohexyl(phenyl)[1-(pyrrolidin-1-ylmethyl)-1H-1,2,4-triazol-5-yl]methanol

HRID 2383377노트

반응식

HRID 2383377 반응식
[N:1]1([CH2:6][N:7]2[CH:11]=[N:10][CH:9]=[N:8]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C([Li])CCC.[CH:17]1([C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:24])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.O>O1CCCC1>[CH:25]1([C:23]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)([C:11]2[N:7]([CH2:6][N:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)[N:8]=[CH:9][N:10]=2)[OH:24])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1

참가 물질

6

반응물 4

HCID 962WaterHCID 12837Cyclohexyl phenyl ketoneHCID 38457621-(pyrrolidin-1-ylmethyl)-1H-1,2,4-triazoleHCID 178418339Butyllithium

생성물 1

HCID 59145963Cyclohexyl(phenyl)[1-(pyrrolidin-1-ylmethyl)-1H-1,2,4-triazol-5-yl]methanol수율 100%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

1-(pyrrolidin-1-ylmethyl)-1H-1,2,4-triazole (Preparation 16, 12.0 g, 78.84 mmol) was dissolved in tetrahydrofuran (120 mL) and the solution cooled to −78° C. n-Butyl lithium (2.5M in hexanes, 34.7 ml, 86.7 mmol) was then added dropwise over 30 mins. After warming to room temperature and stirring for 1 hour the reaction mixture was cooled to −78° C. and a solution of cyclohexyl(phenyl)methanone (16.3 g, 86.7 mmol) in tetrahydrofuran (30 mL) added dropwise. After warming to room temperature over 18 hr, water (100 ml) was added and the solvent removed in vacuo. The residue was partitioned with ethyl acetate (200 ml), the aqueous phase separated and re-extracted with ethyl acetate (2×200 ml). The combined organic layers were dried over magnesium sulphate, filtered and the solvent removed in vacuo to furnish the title compound as a yellow oil, in 100% yield, 27.28 g.

후처리

  1. additionwas then added dropwise over 30 mins
  2. temperaturewas cooled to −78° C.
  3. temperatureAfter warming to room temperature over 18 hr
  4. customthe solvent removed in vacuo
  5. customThe residue was partitioned with ethyl acetate (200 ml)
  6. customthe aqueous phase separated
  7. extractionre-extracted with ethyl acetate (2×200 ml)
  8. dry with materialThe combined organic layers were dried over magnesium sulphate
  9. filtrationfiltered
  10. customthe solvent removed in vacuo

출처 및 근거

ORD 기록
ord-b1872d3100d34d0797f3fdcd3b1c4562
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263623B2

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