Dimethylformamide → Methyl 3-(bis(tert-butoxycarbonyl)amino)-6-pyrrolidin-1-yl-pyrazine-2-carboxylate

HRID 2368380Notes

Reaction equation

HRID 2368380 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C.[C:12]([O:16][C:17]([N:19]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:20]1[C:21]([C:27]([O:29][CH3:30])=[O:28])=[N:22][C:23](Br)=[CH:24][N:25]=1)=[O:18])([CH3:15])([CH3:14])[CH3:13].[NH:38]1[CH2:42][CH2:41][CH2:40][CH2:39]1>[Cu]Br.C1C=C2C=CC(O)=C(C3C4C(=CC=CC=4)C=CC=3O)C2=CC=1.O>[C:12]([O:16][C:17]([N:19]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:20]1[C:21]([C:27]([O:29][CH3:30])=[O:28])=[N:22][C:23]([N:38]2[CH2:42][CH2:41][CH2:40][CH2:39]2)=[CH:24][N:25]=1)=[O:18])([CH3:15])([CH3:14])[CH3:13]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 31268PyrrolidineHCID 86660188Methyl 3-(bis(tert-butoxycarbonyl)amino)-6-bromopyrazine-2-carboxylate

Product 1

HCID 70098560Methyl 3-(bis(tert-butoxycarbonyl)amino)-6-pyrrolidin-1-yl-pyrazine-2-carboxylateYield 75.5%

Reagents, catalysts & solvents 3

HCID 11762BinolCatalystHCID 24593copper(I) bromideCatalystHCID 962WaterSolvent

Procedure

A pre-dried flask was charged with copper(I) bromide (0.35 mg, 2.89 μmol), (R)-(+)-1,1′-bi-2-naphthol (1.66 mg, 5.78 μmol) and cesium carbonate (113 mg, 347 μmol) under argon atmosphere. DMF (0.5 ml), methyl 3-(bis(tert-butoxycarbonyl)amino)-6-bromopyrazine-2-carboxylate (50 mg, 116 μmol) and pyrrolidine (14.3 μl, 174 μmol) were added and the reaction mixture was stirred at r.t. for 1.5 h. The reaction mixture was poured into water (10 ml) and extracted with ethyl acetate. The combined organic layer was washed with brine, dried, evaporated and purified by silica gel chromatography using a heptane/ethyl acetate gradient to yield the product as yellow solid (37 mg, 68%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. customdried
  4. customevaporated
  5. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-55ff57ab65c247099b26c316f681399e
Source dataset
uspto-grants-2014_04
Patent number
US08703768B2

Reaction notes

Loading…