Potassium Carbonate → HCID 57678392, compound

HRID 491464Notes

Reaction equation

HRID 491464 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:19][CH2:18][C:11]2([C:15](=[O:16])[NH:14][C:13](=[O:17])[CH2:12]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:21][CH2:22][O:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][O:25]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]2([C:15](=[O:16])[N:14]([CH2:21][CH2:22][O:23][CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][O:25]3)[C:13](=[O:17])[CH2:12]2)[CH2:18][CH2:19]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 53234195tert-Butyl 1,3-dioxo-2,8-diazaspiro[4.5]decane-8-carboxylate

Product 1

HCID 57678392HCID 57678392, compoundYield 109.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 1,3-dioxo-2,8-diaza-spiro[4.5]decane-8-carboxylic acid tert-butyl ester (1.0 g, 3.7 mmol) in DMF (12 ml), 2-(2-bromoethoxy)-tetrahydro-2H-pyrane (0.62 ml, 4.1 mmol) and potassium carbonate (0.62 g, 4.5 mmol) are added at ambient temperature and the mixture is stirred for overnight at room temperature. The reaction mixture is quenched with water and extracted with ethyl acetate. The combined extracts are washed with brine and dried over sodium sulfate, filtrated. The solvent is evaporated down to give 1.6 g of crude 1,3-dioxo-2-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-2,8-diaza-spiro[4.5]decane-8-carboxylic acid tert-butyl ester.

Workup

  1. additionare added at ambient temperature
  2. customThe reaction mixture is quenched with water
  3. extractionextracted with ethyl acetate
  4. washThe combined extracts are washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltrated
  7. customThe solvent is evaporated down

Sources & evidence

ORD record
ord-7bea876f723a4c87b59f808773e688fa
Source dataset
uspto-grants-2009_05
Patent number
US07531546B2

Reaction notes

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