Ammonia → 3-Azabicyclo[3.2.1]octan-6-one ethylene ketal

HRID 597970Notes

Reaction equation

HRID 597970 reaction equation
CS(O[CH2:6][CH:7]1[CH2:15][CH:14]([CH2:16]OS(C)(=O)=O)[CH2:13][C:8]21[O:12][CH2:11][CH2:10][O:9]2)(=O)=O.[NH3:22]>>[CH2:11]1[O:12][C:8]2([CH2:13][CH:14]3[CH2:15][CH:7]2[CH2:6][NH:22][CH2:16]3)[O:9][CH2:10]1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 574863466,8-Bis(methylsulfonyloxymethyl)-1,4-dioxaspiro[4.4]nonane

Product 1

HCID 597519893-Azabicyclo[3.2.1]octan-6-one ethylene ketalYield 100%

Conditions

Temperature
60 °C

Procedure

6,8-Bis(methanesulfonyloxymethyl)-1,4-dioxaspiro[4.4]nonane (14.90 g, 43.3 mmol) was suspended in aqueous ammonia (35%, 150 ml) and heated for 18 h at 60° C. The reaction was cooled to ambient temperature and concentrated by rotary evaporation. The residue was treated with saturated sodium chloride solution (50 ml) and extracted with chloroform (3×50 ml). The organic extracts were combined, dried over sodium sulfate, filtered and concentrated to yield a brown oil (7.69 g, 100%).

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. concentrationconcentrated by rotary evaporation
  3. additionThe residue was treated with saturated sodium chloride solution (50 ml)
  4. extractionextracted with chloroform (3×50 ml)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-044189f66c8d4f468dedd5b8ce705a2e
Source dataset
uspto-grants-2011_03
Patent number
US07897611B2

Reaction notes

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