(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidine → (S)-tert-butyl (1-(imidazo[1,2-a]pyrazin-8-yl)pyrrolidin-3-yl)carbamate
Reaction equation
[NH:1]1[CH2:5][CH2:4][C@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:2]1.Cl[C:15]1[C:16]2[N:17]([CH:21]=[CH:22][N:23]=2)[CH:18]=[CH:19][N:20]=1>C(NC(C)C)(C)C.CN1C(=O)CCC1.C(OCC)(=O)C>[N:23]1[CH:22]=[CH:21][N:17]2[CH:18]=[CH:19][N:20]=[C:15]([N:1]3[CH2:5][CH2:4][C@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:12])[CH3:11])[CH2:2]3)[C:16]=12Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 100 °C
Procedure
To a solution of (S)-tert-butyl pyrrolidin-3-ylcarbamate (80.2 g, 0.43 mol, 1.1 eq) in 75 mL of diisopropylamine and 34 mL of NMP was added portionwise 8-chloroimidazo[1,2-a]pyrazine (60 g, 0.39 mol, 1 eq). The reaction mixture was heated at 100° C. for 4 h and was then diluted with 1.2 L of ethyl acetate. The organic layer was washed with H2O and brine, dried with Na2SO4 and concentrated to give (S)-tert-butyl (1-(imidazo[1,2-a]pyrazin-8-yl)pyrrolidin-3-yl)carbamate (111.7 g, 0.37 mol, 94%).
Workup
- washThe organic layer was washed with H2O and brine
- dry with materialdried with Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-f3496f511a3049b697373ccff98be8b4
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09169261B2
Reaction notes
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