L-Proline → 2-(2-Aminoethyl)-1-methylpyrrolidine
Reaction equation
N1[C:6]2[CH2:7][CH2:8][NH:9][C:5]=2N=CC=1.[NH:10]1CCC[C@H:11]1[C:12](O)=O.[C:18](C1CCCN1N)#N>>[NH2:10][CH2:11][CH2:12][CH:5]1[CH2:6][CH2:7][CH2:8][N:9]1[CH3:18]Participants
4
Procedure
In more detail, pyrazinopyrrolidine 1A is synthesized via a [3+2] cycloaddition chemistry. Conversion of L-proline 7 to cyano-1-aminopyrrolidine 8 without loss of stereochemistry, followed by reduction provides the chiral 2-aminoethyl-1-methyl pyrrolidine 2A in high yield. CX-3543 was found to have a formulated solubility of approximately 20 mg/mL.
Sources & evidence
- ORD record
- ord-89dfd50a83844116952346f0b1db9973
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07354916B2
Reaction notes
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