Lithium Hydroxide → (2S)-1-(1,3-benzoxazol-2-yl)-2-piperidinecarboxylic acid

HRID 1276159Notes

Reaction equation

HRID 1276159 reaction equation
[OH-].[Li+].[O:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]1[C:18]([O:20]C)=[O:19]>CO>[O:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]1[C:18]([OH:20])=[O:19]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 10220819methyl (2S)-1-(1,3-benzoxazol-2-yl)-2-piperidinecarboxylate

Product 1

HCID 12050655(2S)-1-(1,3-benzoxazol-2-yl)-2-piperidinecarboxylic acidYield 96.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Aqueous lithium hydroxide solution (1N, 51 ml) was added to a solution of methyl (2S)-1-(1,3-benzoxazol-2-yl)-2-piperidinecarboxylate (8.987 g) [see Preparation 2] in methanol (306 ml) at 0° C. The reaction mixture was stirred at room temperature for 18 hours, after which time the solvent was removed under reduced pressure and the residue partitioned between ethyl acetate and water. The aqueous layer was separated and acidified to pH 2 with 2N aqueous hydrochloric acid, the product was extracted with ethyl acetate, dried over magnesium sulphate and the solvent removed under reduced pressure to afford (2S)-1-(1,3-benzoxazol-2-yl)-2-piperidinecarboxylic acid (8.17 g) as a white solid.

Workup

  1. customafter which time the solvent was removed under reduced pressure
  2. customthe residue partitioned between ethyl acetate and water
  3. customThe aqueous layer was separated
  4. extractionthe product was extracted with ethyl acetate
  5. dry with materialdried over magnesium sulphate
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-45f4787847854e78a5e0001798cbb41e
Source dataset
uspto-grants-2000_12
Patent number
US06166011

Reaction notes

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