Hydroxylamine → 8-Benzyl-8-azabicyclo[3.2.1]octan-3-one oxime

HRID 1269753Notes

Reaction equation

HRID 1269753 reaction equation
[NH2:1][OH:2].[CH2:3]([N:10]1[CH:15]2[CH2:16][CH2:17][CH:11]1[CH2:12][C:13](=O)[CH2:14]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)C>[CH2:3]([N:10]1[CH:15]2[CH2:16][CH2:17][CH:11]1[CH2:12][C:13](=[N:1][OH:2])[CH2:14]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 1198468-Benzyl-8-azabicyclo(3.2.1)octan-3-one

Product 1

HCID 132767338-Benzyl-8-azabicyclo[3.2.1]octan-3-one oximeYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 50%-aqueous hydroxylamine solution (182 mg, 2.76 mmol) was added to a solution of 8-benzyl-8-azabicyclo[3.2.1]octan-3-one (538 mg, 2.50 mmol) in ethanol (5 ml) at room temperature and stirred at room temperature for 4 hours. The reaction mixture was concentrated and the resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol) to obtain 8-benzyl-8-azabicyclo[3.2.1]octan-3-one oxime (516 mg, 90%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol)

Sources & evidence

ORD record
ord-9fab08139bb0440b879a6679b3316f16
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

Loading…