L-Proline → 2-(2-Aminoethyl)-1-methylpyrrolidine

HRID 1786152Notes

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

Reactant 3

HCID 145742L-Proline

HCID 21961495HCID 21961495, compound

HCID 69015056HCID 69015056, compound

Product 1

HCID 983882-(2-Aminoethyl)-1-methylpyrrolidine

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-methylpyrrolidine 2A in high yield. CX-3543 was found to have a formulated solubility of approximately 20 mg/mL.

Sources & evidence

ORD record: ord-543a2ceb0ca843d9ab6b33ebfcafa686
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07507727B2

Reaction notes

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