Borane;tetrahydrofuran → 3-(4-Chloro-phenyl)-2-(2-chloro-phenyl)-5-isopropyl-2,4,5,6-tetrahydro-pyrrolo[3,4-c]pyrazole

HRID 1766428Notes

Reaction equation

HRID 1766428 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[N:11]=[C:10]3[C:20](=O)[N:21]([CH:23]([CH3:25])[CH3:24])[CH2:22][C:9]=23)=[CH:4][CH:3]=1.B.C1COCC1>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[N:11]=[C:10]3[CH2:20][N:21]([CH:23]([CH3:25])[CH3:24])[CH2:22][C:9]=23)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 218687853-(4-chloro-phenyl)-2-(2-chloro-phenyl)-5-isopropyl4,5-dihydro-2H-pyrrolo[3,4-c]pyrazol-6-one

Product 1

HCID 114287133-(4-Chloro-phenyl)-2-(2-chloro-phenyl)-5-isopropyl-2,4,5,6-tetrahydro-pyrrolo[3,4-c]pyrazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-(4-chloro-phenyl)-2-(2-chloro-phenyl)-5-isopropyl-4,5-dihydro-2H-pyrrolo[3,4-c]pyrazol-6-one 3A-1 (7 mg, 0.018 mmol) and BH3THF (166 ml, 166 mmol) was stirred at room temperature for 1 hour and at 50° C. for 17 hours. After the reaction mixture was cooled to room temperature, MeOH (5 ml) was added. The reaction mixture was heated under reflux for 2 h, cooled to room temperature, and concentrated in vacuo. The residue was diluted with 4 M HCl/dioxanes (1 ml) and concentrated under vacuum. The residue was dissolved in CH2Cl2 and hexanes were added to precipitate 8A-1 as a colorless solid (2 mg, 27%): +APCl MS (M+H) 372.5; 1H NMR (CD3OD): δ 7.59-7.43 (m, 4H), 7.38 (d, 2H), 7.20 (d, 2H), 4.80-4.65 (m, 2H), 3.91-3.82 (m, 1H), 3.68-3.55 (m, 2H), 1.52 (d, 6H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 2 h
  3. temperaturecooled to room temperature
  4. concentrationconcentrated in vacuo
  5. additionThe residue was diluted with 4 M HCl/dioxanes (1 ml)
  6. concentrationconcentrated under vacuum
  7. dissolutionThe residue was dissolved in CH2Cl2
  8. additionhexanes were added
  9. customto precipitate 8A-1 as a colorless solid (2 mg, 27%)

Sources & evidence

ORD record
ord-a665035972924c4c8efe723413f46abc
Source dataset
uspto-grants-2007_06
Patent number
US07230024B2

Reaction notes

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