benzyl(2S)-1-(5-methyl-1,3-benzoxazol-2-yl)-2-piperidinecarboxylate → (2S)-1-(5-methyl-1,3-benzoxazol-2-yl)-2-piperidinecarboxylic acid

HRID 1635649Notes

Reaction equation

HRID 1635649 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([N:10]3[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]3[C:16]([O:18]CC3C=CC=CC=3)=[O:17])=[N:7][C:6]=2[CH:26]=1>C(O)C.[Pd]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([N:10]3[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]3[C:16]([OH:18])=[O:17])=[N:7][C:6]=2[CH:26]=1

Participants

4

Reactant 1

HCID 54429299benzyl(2S)-1-(5-methyl-1,3-benzoxazol-2-yl)-2-piperidinecarboxylate

Product 1

HCID 53875550(2S)-1-(5-methyl-1,3-benzoxazol-2-yl)-2-piperidinecarboxylic acidYield 99.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

Benzyl (2S)-1-(5-methyl-1,3-benzoxazol-2-yl)-2-piperidinecarboxylate (0.19 g) [see Preparation 17] was dissolved in ethanol (5 ml) and 10% palladium on carbon (0.05 g) was added. The reaction mixture was hydrogenated at 15 psi for 3 hours at room temperature, after which time 10% palladium on carbon (25 mg) was added and the mixture was hydrogenated for a further 1 hr, the catalyst was then filtered off through a plug of arabocel and washed with ethanol. The solvent was removed under reduced pressure to afford (2S)-1-(5-methyl-1,3-benzoxazol-2-yl)-2-piperidinecarboxylic acid (0.14 g) as a solid.

Workup

  1. waitthe mixture was hydrogenated for a further 1 hr
  2. filtrationthe catalyst was then filtered off through a plug of arabocel
  3. washwashed with ethanol
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-57e0f61b8c14462ab85302875aebaf94
Source dataset
uspto-grants-2003_01
Patent number
US06509464B1

Reaction notes

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