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 841947Notes

Reaction equation

HRID 841947 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-b41d8ee663ac4d2885e70b186ac16d2d
Source dataset
uspto-grants-2002_04
Patent number
US06372736B1

Reaction notes

Loading…