Trifluoroacetic acid → HCID 58171579, compound

HRID 1752298Notes

Reaction equation

HRID 1752298 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9]2)=[N:6][CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:12][CH2:11][NH:10][CH2:9]2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58171574HCID 58171574, compound

Product 1

HCID 58171579HCID 58171579, compoundYield 104.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 3-(5-methylpyridin-2-yl)pyrrolidine-1-carboxylate (260 mg, 1.0 mmol) in dry CH2Cl2 (3 mL) was added TFA (2 mL, 20% in CH2Cl2) dropwise at 0° C. The reaction mixture was stirred at rt for 3 h. TLC showed the disappearance of starting material. The reaction mixture was concentrated under vacuum to afford crude 5-methyl-2-(pyrrolidin-3-yl)pyridine (170 mg, 96%), which was used for the next step without purification.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-eea0a534c64d4f50bf968f5e781aaf35
Source dataset
uspto-grants-2015_10
Patent number
US09163012B2

Reaction notes

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