Sodium Hydroxide → (S)-5-((3,4-Dimethoxyphenoxy)methyl)-2-(pyrrolidin-2-yl)oxazole

HRID 710065Notes

Reaction equation

HRID 710065 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][CH:9]=1.Cl.CCOC(C)=O.[OH-].[Na+]>CCOC(C)=O>[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][CH:9]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21866389Hydrogen chloride-ethyl acetate3×HCID 86706778(S)-t-Butyl 2-(5-((3,4-dimethoxyphenoxy)methyl)oxazol-2-yl)pyrrolidine-1-carboxylate

Product 1

HCID 86706779(S)-5-((3,4-Dimethoxyphenoxy)methyl)-2-(pyrrolidin-2-yl)oxazoleYield 71%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To an AcOEt (1 ml) solution of the compound (0.146 g) obtained in Example 19-(5), 4N HCl-AcOEt (0.5 ml) was added and the mixture was stirred at room temperature for 12 hours. After adding 4N HCl-AcOEt (0.5 ml) and stirring for 3 hours, 4N HCl-AcOEt (0.5 ml) was further added and stirring was continued for an hour. After adding an aqueous solution of 2N NaOH and performing extraction with AcOEt, the organic layer was washed with brine, dried (MgSO4), filtered and concentrated to give the titled compound (0.078 g, pale yellow solid.)

Workup

  1. stirringstirring for 3 hours
  2. stirringstirring
  3. waitwas continued for an hour
  4. extractionextraction with AcOEt
  5. washthe organic layer was washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-8ef649c83bf946969e768f5ea10a6a0b
Source dataset
uspto-grants-2015_11
Patent number
US09181229B2

Reaction notes

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