Water → HCID 58996991, compound

HRID 1592611Notes

Reaction equation

HRID 1592611 reaction equation
[CH:1]12[CH:8]([N:9]([CH2:18][C:19]3[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][N:20]=3)[CH2:10][C:11]3[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][N:12]=3)[CH:5]([CH2:6][CH2:7]1)[CH2:4][NH:3][CH2:2]2.C1([O:32][C:33]([NH:35][OH:36])=O)C=CC=CC=1.O>C1COCC1>[OH:36][NH:35][C:33]([N:3]1[CH2:4][CH:5]2[CH:8]([N:9]([CH2:10][C:11]3[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][N:12]=3)[CH2:18][C:19]3[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][N:20]=3)[CH:1]([CH2:7][CH2:6]2)[CH2:2]1)=[O:32]

Participants

5

Reactant 3

HCID 962WaterHCID 148233Phenyl N-hydroxycarbamateHCID 67271896HCID 67271896, compound

Product 1

HCID 58996991HCID 58996991, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (3-aza-bicyclo[3.2.1]oct-8-yl)-bis-(3-methyl-pyridin-2-ylmethyl)-amine (0.064 g, 0.19 mmol) and hydroxylaminecarboxylic acid phenyl ester (PhOCONHOH) (0.058 g, 0.38 mmol) in dry THF (4 mL) was heated at reflux overnight. Water (10 mL) was then added, and the mixture was extracted with EtOAc (20 mL) and CH2Cl2 (2×20 mL). The extracts were combined and dried over anhydrous Na2SO4. After filtration the solvent was removed by evaporation under vacuum, and the residue was purified by flash chromatography on a silica gel column (100:5:4 CH2Cl2/MeOH/NH4OH), affording the product as a white solid (0.056 g, 75%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. extractionthe mixture was extracted with EtOAc (20 mL) and CH2Cl2 (2×20 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationAfter filtration the solvent
  6. customwas removed by evaporation under vacuum
  7. customthe residue was purified by flash chromatography on a silica gel column (100:5:4 CH2Cl2/MeOH/NH4OH)

Sources & evidence

ORD record
ord-08a935de82f643c78d413cc2f48f464b
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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