Ammonium formate → 4-Oxa-1-azaspiro[5.5]undecan-2-one

HRID 383544Notes

Reaction equation

HRID 383544 reaction equation
C([O-])=O.[NH4+].C([O:8][CH2:9][CH2:10][O:11][CH2:12][C:13]1([N+:19]([O-])=O)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)(=O)C>[Pd].[C].CO>[NH:19]1[C:13]2([CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH2:12][O:11][CH2:10][C:9]1=[O:8]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 67520165HCID 67520165, compound

Product 1

HCID 597188884-Oxa-1-azaspiro[5.5]undecan-2-one

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Under the nitrogen gas atmosphere, ammonium formate (5.75 g, 91.1 mmol) and 10% Pd-carbon (4.5 mg) was added in the methanol (90 mL) solution of (1-nitro-cyclohexylmethoxy)-ethyl acetate (4.5 g, 18.2 mmol) which had been obtained in 2), and the mixture was heated and stirred at 50° C. over-night. After that, the mixture was filtered with Celite, the filtrate was concentrated under reduced pressure, the residue was refined with silica gel column chromatography (Highflash 3L, manufactured by Yamazen Corporation, and the mixtures of hexane and ethyl acetate of 5:1, 1:1, and 1:2 in mixing ratio), and an orange-colored crystal of 4-oxa-1-aza-spiro[5.5]-undecan-2-one (1.67 g, 54%) was obtained.

Workup

  1. customhad been obtained in 2), and the mixture
  2. temperaturewas heated
  3. filtrationAfter that, the mixture was filtered with Celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionthe mixtures of hexane and ethyl acetate of 5:1, 1:1, and 1:2 in mixing ratio), and an orange-colored crystal of 4-oxa-1-aza-spiro[5.5]-undecan-2-one (1.67 g, 54%)
  6. customwas obtained

Sources & evidence

ORD record
ord-4194b82e96414067b16e8f8d1c14842f
Source dataset
uspto-grants-2013_02
Patent number
US08367666B2

Reaction notes

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