Hydroxylamine → HCID 59134550, compound

HRID 1804643Notes

Reaction equation

HRID 1804643 reaction equation
[CH2:1]([N:8]1[CH2:14][CH:13]2[C:15](=O)[CH:10]([CH2:11][CH2:12]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:17][OH:18]>C(O)C.O>[CH2:1]([N:8]1[CH2:14][CH:13]2[C:15](=[N:17][OH:18])[CH:10]([CH2:11][CH2:12]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 787HydroxylamineHCID 156391343-Benzyl-3-azabicyclo(3.2.1)octan-8-one

Product 1

HCID 59134550HCID 59134550, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of the title compound of Step A (6.6 g, 30.7 mmol) in ethanol (80 ml) was added hydroxylamine (3.6 ml of a 50% Wt solution in water, 42.9 mmol) and the resulting mixture heated at reflux for 4 h. The cooled reaction mixture was evaporated and the residue triturated with hexanes, filtered and dried to afford the title compound 4.8 g (68%) as a white solid. 1H NMR (CDCl3): 1.76 (m, 2H), 1.97 (m, 2H), 2.40 (d, J 10.1 Hz, 2H), 2.56 (s, 1H), 2.84 (dd, J 10.3 and 3.7 Hz, 1H), 2.91 (dd, J 10.1 and 3.0 Hz, 1H), 3.35 (s, 1H), 3.57 (s, 2H), 7.29 (m, 1H), 7.35 (m, 4H), 8.49 (s, 1H).

Workup

  1. temperature42.9 mmol) and the resulting mixture heated
  2. temperatureat reflux for 4 h
  3. customThe cooled reaction mixture
  4. customwas evaporated
  5. customthe residue triturated with hexanes
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-841b21c526fc49579abd32b63c8f3920
Source dataset
uspto-grants-2013_01
Patent number
US08354403B2

Reaction notes

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