Sodium Hydroxide → 4-Azatricyclo[4.3.1.13,8]undecan-5-one

HRID 963466Notes

Reaction equation

HRID 963466 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[C:2]1=[O:11])[CH2:8]2.O[NH:13]S(O)(=O)=O.[OH-].[Na+]>C(O)=O>[CH:3]12[CH2:9][CH:7]3[CH2:6][CH:5]([CH2:10][CH:1]([CH2:8]3)[C:2](=[O:11])[NH:13]1)[CH2:4]2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 64151AdamantanoneHCID 170246Hydroxysulfamic acid

Product 1

HCID 2866474-Azatricyclo[4.3.1.13,8]undecan-5-oneYield 97.3%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent2×

Procedure

To a solution of 2-adamantanone (2.00 g) in formic acid (10 ml) was added dropwise a suspension of hydroxyamine-O-sulfonic acid (2.26 g) in formic acid (7 ml) under stirring at ambient temperature. The mixture was heated at reflux temperature for 3.5 hours. The reaction mixture was allowed to cool to room temperature, alkalined with 1N sodium hydroxide aqueous solution and extracted with chloroform twice. The combined extracts were washed with water and dried over sodium sulfate. Removal of the solvent gave 2-azatricyclo[4.3.1.14,8 ]undecan-3-one (2.14 g), which was used in a following reaction step without further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for 3.5 hours
  3. temperatureto cool to room temperature
  4. extractionextracted with chloroform twice
  5. washThe combined extracts were washed with water
  6. dry with materialdried over sodium sulfate
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-8951a168708e4731b3029504fae4fb81
Source dataset
uspto-grants-1998_06
Patent number
US05763437

Reaction notes

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