Ethanol → 1-Azatricyclo(3.3.1.1,3,7)decan-4-one

HRID 1770119Notes

Reaction equation

HRID 1770119 reaction equation
[CH2:1]=O.OS(O)(=O)=O.[NH2:8][CH2:9][CH:10]1[CH2:19]C[C:13]2(OCCO2)[CH2:12][CH2:11]1.[CH3:20][CH2:21][OH:22]>>[N:8]12[CH2:13][CH:12]3[CH2:11][CH:10]([CH2:19][CH:20]([C:21]3=[O:22])[CH2:1]1)[CH2:9]2

Participants

5

Reactant 4

HCID 702EthanolHCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 109539781-{1,4-Dioxaspiro[4.5]decan-8-yl}methanamine

Product 1

HCID 1426421-Azatricyclo(3.3.1.1,3,7)decan-4-oneYield 69%

Procedure

Paraformaldehyde (2.2 g), in 320 ml 2% v/v H2SO4, is heated to boiling and 2.7 g (0.016 mole) of 8-aminomethyl-1,4-dioxaspiro[4,5]decane in 20 ml EtOH, is added over 4 hours. This mixture is then heated at reflux for 24 hours. The cooled reaction is washed with dichloromethane, then basified with 10N NaOH and extracted with dichloromethane. The combined extracts are dried over MgSO4 and stripped to dryness, giving 1.68 g (69%) of product.

Workup

  1. temperatureThis mixture is then heated
  2. temperatureat reflux for 24 hours
  3. customThe cooled reaction
  4. washis washed with dichloromethane
  5. extractionextracted with dichloromethane
  6. dry with materialThe combined extracts are dried over MgSO4

Sources & evidence

ORD record
ord-e3d452ac2a7f4245974ba3b2a558f21b
Source dataset
uspto-grants-1995_01
Patent number
US05385912

Reaction notes

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