Ozone → tert-Butyl 1-formyl-2-oxo-8-azaspiro[4.5]decane-8-carboxylate

HRID 8760

Reaction equation

HRID 8760 reaction equation
[O:1]=[O+][O-].[CH:4]([CH:6]1[C:10]2([CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)[CH2:9][CH2:8][C:7]1=[O:23])=C>CO>[CH:4]([CH:6]1[C:10]2([CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])[CH2:14][CH2:15]2)[CH2:9][CH2:8][C:7]1=[O:23])=[O:1]

Participants

4

Reactant 2

HCID 24823OzoneHCID 21983959tert-Butyl 1-vinyl-2-oxo-8-azaspiro[4.5]decane-8-carboxylate

Product 1

HCID 21983936tert-Butyl 1-formyl-2-oxo-8-azaspiro[4.5]decane-8-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ozone was bubbled into a solution of tert-butyl 1-vinyl-2-oxo-8-azaspiro[4.5]decane-8-carboxylate (0.168 g, 0.599 mmol) from Step B in methanol (6 mL) at −70° C. until a blue color persisted. Excess ozone was removed with a stream of nitrogen and then dimethyl sulfide (0.5 mL) was added. The mixture was allowed to warm to room temperature for 1 h and was then concentrated in vacuo without heating to afford the crude title compound which was used directly in the next step.

Workup

  1. customExcess ozone was removed with a stream of nitrogen
  2. additiondimethyl sulfide (0.5 mL) was added
  3. concentrationwas then concentrated in vacuo
  4. temperaturewithout heating

Sources & evidence

ORD record
ord-6fc8772e8a914fc196de9870a1e7a81f
Source dataset
uspto-grants-2006_08
Patent number
US07091211B2

Linked notes

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