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

HRID 1848438Notes

Reaction equation

HRID 1848438 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). LC/MS: [(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-349a551e66c048fa81c5e9aebbcaa349
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

Loading…