Dimethylformamide → Tert-butyl (1-(3-chloropyrazin-2-yl)pyrrolidin-3-yl)carbamate

HRID 907561Notes

Reaction equation

HRID 907561 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[N:6][CH:5]=[CH:4][N:3]=1.C(C1CCN(N)C1)([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=O.C[N:23]([CH:25]=[O:26])[CH3:24]>>[C:12]([O:11][C:25](=[O:26])[NH:23][CH:24]1[CH2:7][CH2:2][N:3]([C:2]2[C:7]([Cl:8])=[N:6][CH:5]=[CH:4][N:3]=2)[CH2:4]1)([CH3:15])([CH3:14])[CH3:13]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 785752,3-DichloropyrazineHCID 21876723Tert-butyl 1-aminopyrrolidine-3-carboxylate

Product 1

HCID 59013776Tert-butyl (1-(3-chloropyrazin-2-yl)pyrrolidin-3-yl)carbamate

Conditions

Temperature
100 °C

Procedure

To a round bottom flask equipped with a magnetic stir bar was added 2,3-Dichloro-pyrazine (3 g, 20.2 mmol) and dry DMF (50 mL). 3-Boc-aminopyrrolidine (8.2 g, 44.5 mmol) was dissolved in dry DMF (50 mL) and added to the round bottom flask. The reaction mixture was allowed to continue to stir overnight at 100° C. LC/MS analysis indicated the desired product as the main component. The reaction mixture was cooled to room temperature and poured on ice. The mixture was extracted with EtOAc and the EtOAc layer was washed with water and brine and dried on sodium sulfate. After removal of solvent in vacuo the desired product [1-(3-Chloro-pyrazin-2-yl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester (6.8 g, 99% yield) was obtained.

Workup

  1. customTo a round bottom flask equipped with a magnetic stir bar
  2. additionadded to the round bottom flask

Sources & evidence

ORD record
ord-0a3e25ed7ef7495a818e15f086d4f264
Source dataset
uspto-grants-2011_09
Patent number
US08013156B2

Reaction notes

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