tert-butyl 2-[(2S)-2-[(benzyloxy)carbonyl]-1-piperidinyl]-1H-1,3-benzimidazole-1-carboxylate → (2S)-1-[1-(tert-butoxycarbonyl)-1H-1,3-benzimidazol-2-yl]-2-piperidinecarboxylic acid

HRID 412669Notes

Reaction equation

HRID 412669 reaction equation
C([O:8][C:9]([C@@H:11]1[CH2:16][CH2:15][CH2:14][CH2:13][N:12]1[C:17]1[N:21]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:20]2[CH:29]=[CH:30][CH:31]=[CH:32][C:19]=2[N:18]=1)=[O:10])C1C=CC=CC=1>[Pd].C(O)C>[C:25]([O:24][C:22]([N:21]1[C:20]2[CH:29]=[CH:30][CH:31]=[CH:32][C:19]=2[N:18]=[C:17]1[N:12]1[CH2:13][CH2:14][CH2:15][CH2:16][C@H:11]1[C:9]([OH:10])=[O:8])=[O:23])([CH3:28])([CH3:26])[CH3:27]

Participants

4

Reactant 1

HCID 59063194tert-butyl 2-[(2S)-2-[(benzyloxy)carbonyl]-1-piperidinyl]-1H-1,3-benzimidazole-1-carboxylate

Product 1

HCID 59063201(2S)-1-[1-(tert-butoxycarbonyl)-1H-1,3-benzimidazol-2-yl]-2-piperidinecarboxylic acidYield 98.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% w/w Palladium on carbon (300 mg) was added to a solution of tert-butyl 2-[(2S)-2-[(benzyloxy)carbonyl]-1-piperidinyl]-1H-1,3-benzimidazole-1-carboxylate (900 mg) [see Preparation 47] in ethanol (30 ml). The reaction mixture was hydrogenated at 103.5 kPa (15 psi) at room temperature for 18 hours. The catalyst was then filtered off and the solvent removed under reduced pressure to afford (2S)-1-[1-(tert-butoxycarbonyl)-1H-1,3-benzimidazol-2-yl]-2-piperidinecarboxylic acid (700 mg) as a white foam.

Workup

  1. filtrationThe catalyst was then filtered off
  2. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-c353a53b66d44e0e953e3ee8aa3d560b
Source dataset
uspto-grants-2003_05
Patent number
US06562964B1

Reaction notes

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