Sodium Carbonate → HCID 10445156, compound

HRID 233666Notes

Reaction equation

HRID 233666 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[NH2:7][CH:8]1[CH2:12][C:11]2([CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)[O:10][CH:9]1[CH3:19].C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1>[CH2:5]([O:4][C:2](=[O:3])[NH:7][CH:8]1[CH2:12][C:11]2([CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)[O:10][CH:9]1[CH3:19])[CH3:6]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 10928Ethyl chloroformateHCID 9989940HCID 9989940, compound

Product 1

HCID 10445156HCID 10445156, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Ethyl chloroformate was added to 3-Amino-2,8-dimethyl-1-oxa-8-azaspiro[4.5]decane (1 g 5.4 mmol) in THF (20 ml). An additional 20 ml of THF were added and the reaction was stirred for 2 hours at room temperature. The THF solution was mixed with saturated sodium carbonate solution and the THF layer was separated, dried and evaporated to give a product which was purified by chromatography on silica gel and eluting with 5-10% ammoniated MeOH/CHCl3. The major fraction was converted to the fumaric acid salt in ether but a solid could not be obtained. The salt was neutralized with aqueous alkali and the base was extracted into methylene chloride. Concentration of the methylene chloride afforded the title carbamate compound as an oil.

Workup

  1. customthe THF layer was separated
  2. customdried
  3. customevaporated
  4. customto give a product which
  5. customwas purified by chromatography on silica gel
  6. washeluting with 5-10% ammoniated MeOH/CHCl3
  7. customa solid could not be obtained
  8. extractionthe base was extracted into methylene chloride

Sources & evidence

ORD record
ord-8bc4812f2568423ba5c5f77cab37d046
Source dataset
uspto-grants-1997_01
Patent number
US05594000

Reaction notes

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