Water → HCID 58996991, compound

HRID 251199Notes

Reaction equation

HRID 251199 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%). 1H NMR (CDCl3) δ 1.51-1.58 (m, 2H), 1.74-1.77 (m, 2H), 2.14 (s, 6H), 2.25 (s, br. 2H), 3.15 (t, 1H, J=4.2 Hz), 3.24-3.29 (m, 2H), 3.37-3.42 (m, 2H), 3.96 (s, 4H), 6.93 (s, br. 1H), 6.98 (dd, 2H, J=4.8, 7.5 Hz), 7.25 (d, 2H, J=7.5 Hz), 8.33 (d, 2H, J=4.8 Hz); 13C NMR (CDCl3) δ 18.93, 26.08, 35.82, 44.58, 57.64, 67.11, 122.19, 132.69, 137.86, 146.39, 157.51, 163.07. ES-MS m/z 396 (M+H). Anal. Calcd. for C22H29N5O2.0.4CH2Cl2: C, 62.65; H, 6.99; N, 16.31. Found: C, 62.50; H, 7.35; N, 16.10.

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-eafa1dd2d5e84cdd9a6a9e95148698fd
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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