Phthalic Acid → Benzyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylate

HRID 47308

Reaction equation

HRID 47308 reaction equation
[CH2:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][CH2:3]1.C(O)(=O)C1C(=CC=CC=1)C(O)=[O:22].C(=O)(O)[O-].[Na+]>CO>[O:22]1[C:2]2([CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[O:9])[CH2:4][CH2:3]2)[CH2:1]1

Participants

5

Reactant 3

HCID 1017Phthalic AcidHCID 516892Sodium BicarbonateHCID 15519136Benzyl 4-methylidenepiperidine-1-carboxylate

Product 1

HCID 13016598Benzyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylateYield 71.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

14.7 g of benzyl 4-methylene-1-piperidinecarboxylate was dissolved in 300 ml methanol, 20.4 g of phthalic acid monoperacid magnesium salt and 13.3 g of sodium bicarbonate were added thereto, and the mixture was stirred at room temperature for 7.5 hr. The reaction solution was evaporated. Ethyl acetate was added to the resulting residue which was then washed with water and brine, dried over anhydrous magnesium sulfate, and then filtered. The filtrate was evaporated, and then subjected to silica gel column chromatography to give 11.3 g of benzyl 1-oxa-6-azaspiro[2.5]octane-6-carboxylate.

Workup

  1. customThe reaction solution was evaporated
  2. additionEthyl acetate was added to the resulting residue which
  3. washwas then washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-9e9da809d2ca4d10a326e91be1998ec9
Source dataset
uspto-grants-2004_03
Patent number
US06699870B2

Linked notes

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