Tetrahydrofuran → HCID 58982049, compound

HRID 1182159Notes

Reaction equation

HRID 1182159 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:27][CH2:26][C:11]2([C:15](=[O:16])[N:14]([CH2:17][C:18]3[CH:23]=[CH:22][C:21](SC)=[CH:20][CH:19]=3)[CH2:13][CH2:12]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O[O:29][S:30]([O-:32])=O.[K+].[OH-].[Na+].[CH2:36]1COCC1>O>[C:1]([O:5][C:6]([N:8]1[CH2:27][CH2:26][C:11]2([C:15](=[O:16])[N:14]([CH2:17][C:18]3[CH:19]=[CH:20][C:21]([S:30]([CH3:36])(=[O:32])=[O:29])=[CH:22][CH:23]=3)[CH2:13][CH2:12]2)[CH2:10][CH2:9]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 23707502Potassium hydroxy sulfiteHCID 58981995HCID 58981995, compound

Product 1

HCID 58982049HCID 58982049, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 7.73 g (19.8 mmol) of 2-(4-methylsulfanylbenzyl)-1-oxo-2,8-diaza-spiro[4.5]decane-8-carboxylic acid tert-butyl ester, previously dissolved in 100 mL of THF, were added 18.2 g (29.7 mmol) of Oxone® in 100 mL of water. The reaction mixture was agitated overnight at room temperature. Then 100 mL of 1N aqueous solution of sodium hydroxide were added and the solution was extracted with DCM (2×200 mL). The combined organic layers were dried (Na2SO4), filtered and evaporated under reduced pressure to yield 6.62 g (79.1%) of 2-(4-methanesulfonylbenzyl)-1-oxo-2,8-diaza-spiro[4.5]decane-8-carboxylic acid tert-butyl ester as a white solid.

Workup

  1. extractionthe solution was extracted with DCM (2×200 mL)
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-e1d1458253754b94be03b0038f78bf69
Source dataset
uspto-grants-2007_10
Patent number
US07288548B2

Reaction notes

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