Hydrochloric Acid → 6-Butyl-8-[(3R)-3-pyrrolidinyloxy]quinoline

HRID 1363008Notes

Reaction equation

HRID 1363008 reaction equation
[CH2:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([O:15][C@@H:16]3[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17]3)[CH:14]=1)[N:11]=[CH:10][CH:9]=[CH:8]2)[CH2:2][CH2:3][CH3:4].Cl>O1CCOCC1>[CH2:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([O:15][C@@H:16]3[CH2:20][CH2:19][NH:18][CH2:17]3)[CH:14]=1)[N:11]=[CH:10][CH:9]=[CH:8]2)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 669219361,1-dimethylethyl (3R)-3-[(6-butyl-8-quinolinyl)oxy]-1-pyrrolidinecarboxylate2×

Product 1

HCID 669217306-Butyl-8-[(3R)-3-pyrrolidinyloxy]quinoline

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

This was prepared in an analogous manner to Intermediate 4, using 1,1-dimethylethyl (3R)-3-[(6-butyl-8-quinolinyl)oxy]-1-pyrrolidinecarboxylate (for example, as prepared for Intermediate 9) and 4 M hydrogen chloride in 1,4-dioxane instead of trifluoroacetic acid for 45 min. LCMS RT=2.46 min, ES+ve m/z 271 (M+H)+.

Workup

  1. customfor 45 min

Sources & evidence

ORD record
ord-1e8a367010784ed7bf6362ff9e20f5ee
Source dataset
uspto-grants-2011_02
Patent number
US07884114B2

Reaction notes

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