Thiophenol → Ethyl 8-oxa-1-azaspiro[4.5]decane-2-carboxylate

HRID 454450Notes

Reaction equation

HRID 454450 reaction equation
[N+](C1C=CC(S([N:13]2[C:17]3([CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[CH2:16][CH2:15][CH:14]2[C:23]([O:25][CH2:26][CH3:27])=[O:24])(=O)=O)=CC=1)([O-])=O.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1.C1(S)C=CC=CC=1>C(#N)C>[NH:13]1[C:17]2([CH2:18][CH2:19][O:20][CH2:21][CH2:22]2)[CH2:16][CH2:15][CH:14]1[C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

6

Reactant 4

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 58313109Ethyl 1-[(4-nitrophenyl)sulfonyl]-8-oxa-1-azaspiro[4.5]decane-2-carboxylate

Product 1

HCID 58313084Ethyl 8-oxa-1-azaspiro[4.5]decane-2-carboxylateYield 90%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of ethyl 1-[(4-nitrophenyl)sulfonyl]-8-oxa-1-azaspiro[4.5]decane-2-carboxylate (165) (1.47 g, 3.7 mmol) in anhydrous acetonitrile (25 mL) was added potassium carbonate (0.76 g, 5.5 mmol), 18-crown-6 (0.2 g, 0.7 mmol) and thiophenol (0.6 mL. 5.5 mmol) and the reaction stirred at room temperature for 18 h. The reaction was concentrated in vacuo and the residue dissolved in 0.1 N HCl. The aqueous layer was extracted twice with EtOAc and the organic layer was discarded. The aqueous layer was treated with solid potassium carbonate until the solution gave blue pH paper. It was extracted with 15% isopropanol/dichloromethane (3×) and the organic layer dried over sodium sulfate and concentrated in vacuo to afford the title compound as a clear oil (0.71 g, 90% yield).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. dissolutionthe residue dissolved in 0.1 N HCl
  3. extractionThe aqueous layer was extracted twice with EtOAc
  4. additionThe aqueous layer was treated with solid potassium carbonate until the solution
  5. customgave blue pH paper
  6. extractionIt was extracted with 15% isopropanol/dichloromethane (3×)
  7. dry with materialthe organic layer dried over sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-38a1774f861d461b86a218c3a441609e
Source dataset
uspto-grants-2013_07
Patent number
US08492554B2

Reaction notes

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