Hydrochloric Acid → 3,3-Dimethyl-1-(9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)-2-butanone

HRID 411164Notes

Reaction equation

HRID 411164 reaction equation
[CH3:1][C:2]([CH3:23])([CH3:22])[C:3](=[O:21])[CH2:4][N:5]1[CH2:12][CH:11]2[O:13][CH:7]([CH2:8][N:9](C(OC(C)(C)C)=O)[CH2:10]2)[CH2:6]1.Cl.C(#N)C.C([O-])([O-])=O.[K+].[K+]>C(OCC)(=O)C>[CH3:1][C:2]([CH3:23])([CH3:22])[C:3](=[O:21])[CH2:4][N:5]1[CH2:12][CH:11]2[O:13][CH:7]([CH2:8][NH:9][CH2:10]2)[CH2:6]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 18540396Tert-butyl 7-(3,3-dimethyl-2-oxobutyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate

Product 1

HCID 185403983,3-Dimethyl-1-(9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)-2-butanoneYield 86.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of tert-butyl 7-(3,3-dimethyl-2-oxobutyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate (from step (i) above; 0.265 g, 0.812 mmol) in ethyl acetate (10 mL) was treated, at 0° C., with ethyl acetate saturated with gaseous hydrochloric acid. The mixture was stirred at 0° C. for 5 h, and then evaporated. Acetonitrile (15 mL) and K2CO3 (1 g, 7.2 mmol) were added, and the mixture was stirred overnight before being filtered and evaporated to yield 0.159 g (86%) of the sub-title compound.

Workup

  1. customevaporated
  2. stirringthe mixture was stirred overnight
  3. filtrationbefore being filtered
  4. customevaporated

Sources & evidence

ORD record
ord-f45172967c2547d7be0bc3654dffcc31
Source dataset
uspto-grants-2003_05
Patent number
US06559143B1

Reaction notes

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