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

HRID 47310

Reaction equation

HRID 47310 reaction equation
[CH2:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.C(O)(=O)C1C(=CC=CC=1)C(O)=[O:19].C(=O)(O)[O-].[Na+]>CO>[O:19]1[C:2]2([CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]2)[CH2:1]1

Participants

5

Reactant 3

HCID 1017Phthalic AcidHCID 516892Sodium BicarbonateHCID 27568081-Boc-4-Methylenepiperidine

Product 1

HCID 22135564tert-Butyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylateYield 83.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

13.5 g of tert-butyl 4-methylene-1-piperidinecarboxylate was dissolved in 300 ml methanol, and 28.3 g phthalic acid monoperacid magnesium salt and 8.62 g sodium bicarbonate were added thereto, and the mixture was stirred at room temperature for 1 day. The reaction solution was filtered through Celite, and the resulting filtrate 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 subjected to silica gel column chromatography to give 12.2 g of tert-butyl 1-oxa-6-azaspiro[2.5]octane-6-carboxylate.

Workup

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

Sources & evidence

ORD record
ord-88932765c1a24248bf34df8e7ab3a97d
Source dataset
uspto-grants-2004_03
Patent number
US06699870B2

Linked notes

Loading…