Ethanol → 1-methylcyclopropyl 4-[(1R,2S)-2-(2-{[3-methyl-5-(1H-tetrazol-1 yl)pyridin-2-yl]oxy}ethyl)cyclopropyl]piperidine-1-carboxylate

HRID 1850752Notes

Reaction equation

HRID 1850752 reaction equation
[CH3:1][C:2]1[C:3]([O:13][CH2:14][CH2:15][C@@H:16]2[CH2:18][C@@H:17]2[CH:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][CH2:28][C:29]3C=CC=C[CH:30]=3)=[O:26])[CH2:21][CH2:20]2)=[N:4][CH:5]=[C:6]([N:8]2[CH:12]=[N:11][N:10]=[N:9]2)[CH:7]=1.[CH3:35]CO>[Pd]>[CH3:1][C:2]1[C:3]([O:13][CH2:14][CH2:15][C@@H:16]2[CH2:18][C@@H:17]2[CH:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]3([CH3:35])[CH2:30][CH2:29]3)=[O:26])[CH2:21][CH2:20]2)=[N:4][CH:5]=[C:6]([N:8]2[CH:12]=[N:11][N:10]=[N:9]2)[CH:7]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 66563379benzyl 4-[(1R,2S)-2-(2-{[3-methyl-5-(1H-tetrazol-1-yl)pyridin-2-yl]oxy}ethyl)cyclopropyl]piperidine-1-carboxylate

Product 1

HCID 708563071-methylcyclopropyl 4-[(1R,2S)-2-(2-{[3-methyl-5-(1H-tetrazol-1 yl)pyridin-2-yl]oxy}ethyl)cyclopropyl]piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of benzyl 4-[(1R,2S)-2-(2-{[3-methyl-5-(1H-tetrazol-1-yl)pyridin-2-yl]oxy}ethyl)cyclopropyl]piperidine-1-carboxylate (920 mg, 1.99 mmol) in 5 ml of EtOH was treated with 200 mg of Pd/C under a balloon of H2 gas for 3.5 hours. The suspension was filtered through a plug of celite and the filtrate was concentrated to afford the title compound as a crude product to be used for the next step. LC/MS (m/z): 329 (M+H)+.

Workup

  1. filtrationThe suspension was filtered through a plug of celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-28803b7ef2004006a477ed16769c6171
Source dataset
uspto-grants-2015_02
Patent number
US08957062B2

Reaction notes

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