Methanol → HCID 67387381, 화합물

HRID 889393노트

반응식

HRID 889393 반응식
B.O1CCCC1.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:18]([CH:19]([CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[C:20](O)=[O:21])=[C:17]3[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:16]3=[N:15]2)=[CH:10][CH:9]=1.CO.O>C1COCC1>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([N:14]2[C:18]([CH:19]([CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[CH2:20][OH:21])=[C:17]3[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:16]3=[N:15]2)=[CH:12][CH:13]=1

참가 물질

6

반응물 4

HCID 887MethanolHCID 962WaterHCID 2723981Borane;tetrahydrofuranHCID 67387113[2-(4-Chloro-phenyl)-2,4,5,6,7,8-hexahydro-cycloheptapyrazol-3-yl]-cyclohexyl-acetic acid

생성물 1

HCID 67387381HCID 67387381, 화합물수율 51%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Borane-tetrahydrofuran complex (920 ul, 920 umol; 1 M solution in THF) was added to an ice cold solution of [2-(4-chloro-phenyl)-2,4,5,6,7,8-hexahydro-cycloheptapyrazol-3-yl]-cyclohexyl-acetic acid (143 mg, 370 umol; example 9.3) in THF (1.5 ml). The solution was stirred at ambient temperature for 14 h and cooled to 0° C. Methanol (1.5 ml) and water (1.5 ml) were added and the mixture was extracted two times with iPrOAc. The combined extracts were washed with brine and dried over Na2SO4. The solvent was removed under reduced pressure, the residue was dissolved in methanol (4.5 ml) and heated under reflux conditions for 30 min. The solvent was removed under reduced pressure and the residue purified by preparative thin layer chromatography (silica gel, iPrOAc/heptane) to obtain the title compound (70 mg, 188 umol; 51%) as colorless oil. MS: m/e=373.2 [M+H+].

후처리

  1. temperaturecooled to 0° C
  2. extractionthe mixture was extracted two times with iPrOAc
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed under reduced pressure
  6. dissolutionthe residue was dissolved in methanol (4.5 ml)
  7. temperatureheated under reflux conditions for 30 min
  8. customThe solvent was removed under reduced pressure
  9. customthe residue purified by preparative thin layer chromatography (silica gel, iPrOAc/heptane)

출처 및 근거

ORD 기록
ord-1b4ed92745654b3fb3de2d357768fd85
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08252826B2

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