1,4-Dioxa-10-azadispiro[4.2.4^{8}.2^{5}]tetradecan-11-one → 2-Azaspiro[4.5]decane-3,8-dione

HRID 1505692Notes

Reaction equation

HRID 1505692 reaction equation
O1[C:5]2([CH2:15][CH2:14][C:8]3([CH2:12][C:11](=[O:13])[NH:10][CH2:9]3)[CH2:7][CH2:6]2)[O:4]CC1>Cl>[CH2:9]1[C:8]2([CH2:7][CH2:6][C:5](=[O:4])[CH2:15][CH2:14]2)[CH2:12][C:11](=[O:13])[NH:10]1

Participants

3

Reactant 1

HCID 577954141,4-Dioxa-10-azadispiro[4.2.4^{8}.2^{5}]tetradecan-11-one

Product 1

HCID 577955102-Azaspiro[4.5]decane-3,8-dioneYield 92%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 1,4-dioxa-10-azadispiro[4.2.4.2]tetradecan-11-one (10.5 g, 49.8 mmol) in aq.HCl (2N, 20 mL) was stirred at RT for 2 h. The reaction mixture was then concentrated under reduced pressure and diluted with water. It was extracted with ethyl acetate (Three times) and the combined organic phases were washed with water, brine, dried over sodium sulfate, filtered and concentrated. Purification by flash chromatography on silica (Pet.Ether:EtOAc) afforded the title compound as a white solid (7.5 g, 92%). 1H NMR (400 MHz, DMSO-d6) δ 7.58 (m, 1H), 3.15-3.15 (s, 2H), 2.30 (s, 4H), 2.28-2.25 (m, 2H), 1.82-1.79 (m, 4H).

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. additiondiluted with water
  3. extractionIt was extracted with ethyl acetate (Three times)
  4. washthe combined organic phases were washed with water, brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by flash chromatography on silica (Pet.Ether:EtOAc)

Sources & evidence

ORD record
ord-4efee3957e73407a92baf910e807ce65
Source dataset
uspto-grants-2015_12
Patent number
US09216991B2

Reaction notes

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