Acetic Acid → 4-(2,8-diazaspiro[4.5]decan-2-yl)furan-2(5H)-one

HRID 1501757Notes

Reaction equation

HRID 1501757 reaction equation
[O:1]1[CH2:5][C:4](=O)[CH2:3][C:2]1=[O:7].[CH2:8]1[C:12]2([CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]2)[CH2:11][CH2:10][NH:9]1.C(O)(=O)C>CC(O)C>[CH2:8]1[C:12]2([CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH2:11][CH2:10][N:9]1[C:4]1[CH2:5][O:1][C:2](=[O:7])[CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 521261Tetronic acidHCID 23282900tert-Butyl 2,8-diazaspiro(4.5)decane-8-carboxylate

Product 1

HCID 867094464-(2,8-diazaspiro[4.5]decan-2-yl)furan-2(5H)-one

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Commercially available furan-2,4(3H,5H)-dione (0.433 g, 4.33 mmol) and tert-butyl 2,8-diazaspiro[4.5]decane-8-carboxylate (commercially available from multiple vendors, acetic acid salt, 0.65 g, 2.2 mmol) in 20 mL i-PrOH was heated in a sealed tube at 110° C. overnight. The solid was filtered off and the filtrate was concentrated under vacuum. The residue was dissolved in 30 mL DCM and 5 mL TFA and stirred at rt for 1 h. The mixture was concentrated, and the residue was purified by preparative TLC (10% 2N NH3 in methanol-DCM). LCMS: [(M+1)]+=223

Workup

  1. filtrationThe solid was filtered off
  2. concentrationthe filtrate was concentrated under vacuum
  3. dissolutionThe residue was dissolved in 30 mL DCM
  4. concentrationThe mixture was concentrated
  5. customthe residue was purified by preparative TLC (10% 2N NH3 in methanol-DCM)

Sources & evidence

ORD record
ord-fd332dbc22854a6dbac43180a6f3756b
Source dataset
uspto-grants-2015_12
Patent number
US09206198B2

Reaction notes

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