Ammonium formate → HCID 69999996, compound

HRID 1634793Notes

Reaction equation

HRID 1634793 reaction equation
C([O:3][C:4](=[O:41])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]([N:14]2[CH2:19][CH2:18][CH:17]([CH2:20][NH:21][CH2:22][C@H:23]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH2:24][O:25][C:26]3[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=3)[CH2:16][CH2:15]2)=[O:13])[CH:6]=1)C.C([O-])=O.[NH4+]>CO.[Pd]>[CH2:34]([O:33][C@H:23]([CH2:24][O:25][C:26]1[CH:27]=[CH:28][C:29]([OH:32])=[CH:30][CH:31]=1)[CH2:22][NH:21][CH2:20][CH:17]1[CH2:16][CH2:15][N:14]([C:12]([NH:11][C:7]2[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=2)[C:4]([OH:41])=[O:3])=[O:13])[CH2:19][CH2:18]1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 69999837HCID 69999837, compound

Product 1

HCID 69999996HCID 69999996, compoundYield 24.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-[(4-{[(2S)-2-benzyloxy-3-(4-hydroxy-phenoxy)-propylamino]-methyl}-piperidine-1-carbonyl)-amino]-benzoic acid ethyl ester (0.112 g, 0.43 mmol) and ammonium formate (0.063 g, 1 mmol) in 5 mL of methanol over 0.112 g of 10% palladium on carbon was stirred at ambient temperature overnight. The catalyst was filtered (solka floc) and the filtrate concentrated in vacuo. Trituration of the crude solid foam with Et2O provided 0.057 g of the title compound as an off-white solid.

Workup

  1. filtrationThe catalyst was filtered (solka floc)
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-9bbb27e0505b42bc90b2ca4e14481e5f
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

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