Hydrochloric Acid → 8-Benzyl-8-azabicyclo(3.2.1)octan-3-one

HRID 342498

Reaction equation

HRID 342498 reaction equation
CO[CH:3]1[CH2:7][CH2:6][CH:5](OC)[O:4]1.[CH2:10]([C:17](O)=O)[C:11](CC(O)=O)=O.[CH2:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.Cl>O>[CH2:20]([N:27]1[CH:6]2[CH2:5][CH2:17][CH:10]1[CH2:11][C:3](=[O:4])[CH2:7]2)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7504BenzylamineHCID 68328Acetonedicarboxylic acidHCID 790982,5-Dimethoxytetrahydrofuran

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

This was prepared according to the reported method (Chem. Abs., 1958, 53, 432e). A mixture of 2,5-dimethoxytetrahydrofuran (13 ml, 0.1 mol), 2 drops of c-HCl and water (10 ml) was stirred at room temperature for 1 h, then treated with water(10 ml), acetone-1,3-dicarboxylic acid (14.6 g, 0.1 mol), and benzylamine (10.9 ml, 0.1 mol). After the initial foaming had subsided, the pH was adjusted to 5 with 1N HCl, and stirring was continued for 14 h. The reaction mixture was adjusted to pH 1, washed with ethyl acetate, filtered through celite, and then adjusted to pH 12 with NaOH, and extracted with ethyl acetate. The extract was dried over Na2SO4 and concentrated to afford 14.5 g (67% crude) of an oil, which was used for next reaction without further purification.

Workup

  1. customThis was prepared
  2. stirringstirring
  3. waitwas continued for 14 h
  4. washwashed with ethyl acetate
  5. filtrationfiltered through celite
  6. extractionextracted with ethyl acetate
  7. dry with materialThe extract was dried over Na2SO4
  8. concentrationconcentrated
  9. customto afford 14.5 g (67% crude) of an oil, which
  10. customwas used for next reaction without further purification

Sources & evidence

ORD record
ord-82e41779e80b4e1d91deff0809760f5e
Source dataset
uspto-grants-1999_01
Patent number
US05859011

Linked notes

Loading…