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

HRID 1685492Notes

Reaction equation

HRID 1685492 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-00bbcb97a86843e88b40227983516b8d
Source dataset
uspto-grants-2012_04
Patent number
US08148408B2

Reaction notes

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