Hydrogen chloride-ethyl acetate → (S)-2-((3,4-Dimethoxyphenoxy)methyl)-5-(pyrrolidin-2-yl)-1,3,4-oxadiazole hydrochloride

HRID 710041Notes

Reaction equation

HRID 710041 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:25]=[CH:26][C:27]=1[O:28][CH3:29])[O:6][CH2:7][C:8]1[O:12][C:11]([C@@H:13]2[CH2:17][CH2:16][CH2:15][N:14]2C(OC(C)(C)C)=O)=[N:10][N:9]=1.[ClH:30].CCOC(C)=O>CCOC(C)=O>[ClH:30].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:25]=[CH:26][C:27]=1[O:28][CH3:29])[O:6][CH2:7][C:8]1[O:12][C:11]([C@@H:13]2[CH2:17][CH2:16][CH2:15][NH:14]2)=[N:10][N:9]=1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 86706751(S)-t-Butyl 2-(5-((3,4-dimethoxyphenoxy)methyl)-1,3,4-oxadiazol-2-yl)pyrrolidine-1-carboxylate

Product 1

HCID 86706752(S)-2-((3,4-Dimethoxyphenoxy)methyl)-5-(pyrrolidin-2-yl)-1,3,4-oxadiazole hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To an AcOEt (200 ml) solution of the compound (42.0 g) obtained in Example 8-(2), 4N HCl-AcOEt solution (200 ml) was added and the mixture was stirred at room temperature for 4 hours. The solvent was distilled off under reduced pressure to give a crude form of the titled compound (35.0 g).

Workup

  1. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-e40d28dc04aa4f218732df29a087f4cd
Source dataset
uspto-grants-2015_11
Patent number
US09181229B2

Reaction notes

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