Methanol → HCID 67387381, compound

HRID 889393Notes

Reaction equation

HRID 889393 reaction equation
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

Participants

6

Reactant 4

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

Product 1

HCID 67387381HCID 67387381, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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+].

Workup

  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)

Sources & evidence

ORD record
ord-1b4ed92745654b3fb3de2d357768fd85
Source dataset
uspto-grants-2012_08
Patent number
US08252826B2

Reaction notes

Loading…