2,6-Dichloropyrazine → (3aR,6aS)-tert-butyl 5-(6-chloropyrazin-2-yl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate

HRID 240493Notes

Reaction equation

HRID 240493 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[CH2:9]1[C@@H:13]2[CH2:14][NH:15][CH2:16][C@@H:12]2[CH2:11][N:10]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].C(N(CC)C(C)C)(C)C>CS(C)=O.O>[Cl:8][C:4]1[N:3]=[C:2]([N:15]2[CH2:14][C@@H:13]3[CH2:9][N:10]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:11][C@@H:12]3[CH2:16]2)[CH:7]=[N:6][CH:5]=1

Participants

6

Reactant 3

HCID 785042,6-DichloropyrazineHCID 81531DiisopropylethylamineHCID 1514452Cis-2-boc-hexahydropyrrolo[3,4-C]pyrrole

Product 1

HCID 86635809(3aR,6aS)-tert-butyl 5-(6-chloropyrazin-2-yl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylateYield 89.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

2,6-dichloropyrazine (1.02 g, 6.85 mmol) was dissolved in DMSO (7 mL). The product from Example 1C (1.61 g, 7.58 mmol) and N,N-diisopropylethylamine (1.5 mL, 8.61 mmol) were added to the reaction mixture. The reaction was stirred at ambient temperature for 23 h. The reaction was diluted with water (200 mL) and extracted with CH2Cl2 (4×100 mL). The organic extracts were combined and washed with and brine (150 mL), dried over MgSO4, filtered and concentrated under vacuum. The residue was purified by silica gel chromatography (EtOAc, Rf=0.38) to afford the title compound as a white solid (1.99 g, 89%). MS (DCI/NH3) m/z 325 (M+H)+.

Workup

  1. extractionextracted with CH2Cl2 (4×100 mL)
  2. washwashed with and brine (150 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by silica gel chromatography (EtOAc, Rf=0.38)

Sources & evidence

ORD record
ord-9fc50a5aabb543bea2994068ada2fa07
Source dataset
uspto-grants-2014_02
Patent number
US08648084B2

Reaction notes

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