Triethylamine → HCID 74043786, compound

HRID 233664Notes

Reaction equation

HRID 233664 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:17][CH2:16][C:9]2([O:13][CH:12]([CH3:14])[C:11](=O)[CH2:10]2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].C(N(CC)CC)C.Cl.[NH2:26][OH:27]>C(O)C>[CH2:1]([O:3][C:4]([N:6]1[CH2:17][CH2:16][C:9]2([O:13][CH:12]([CH3:14])[C:11](=[N:26][OH:27])[CH2:10]2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 4588469ethyl 2-methyl-3-oxo-1-oxa-8-azaspiro[4.5]decane-8-carboxylate

Product 1

HCID 74043786HCID 74043786, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

8-Ethoxycarbonyl-2-methyl-1-oxa-8-azaspiro [4.5 ]decan-3-one (20 g, 0.083 mol) was dissolved in absolute ethanol (1 L) and combined with triethylamine (11.5 ml) and hydroxylamine hydrochloride (5.7 g). The mixture was stirred at room temperature overnight. The ethanol was evaporated in vacuo and the residue was stirred with ether. The insoluble solids were filtered and the ether filtrate was evaporated. The residual oxime was purified by chomatography on silica gel and elution with ammoniated 2-10% MeOH/CHCl3. Evaporation of the solvents afforded the oxime, 11.5 g.

Workup

  1. customThe ethanol was evaporated in vacuo
  2. stirringthe residue was stirred with ether
  3. filtrationThe insoluble solids were filtered
  4. customthe ether filtrate was evaporated
  5. customThe residual oxime was purified by chomatography on silica gel and elution with ammoniated 2-10% MeOH/CHCl3
  6. customEvaporation of the solvents

Sources & evidence

ORD record
ord-1398110263c94ba1b859a00c3558815e
Source dataset
uspto-grants-1997_01
Patent number
US05594000

Reaction notes

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