Triethylamine → tert-Butyl 2-[(methylsulfonyl)oxy]-6-azaspiro[3.4]octane-6-carboxylate

HRID 336525Notes

Reaction equation

HRID 336525 reaction equation
C(N(CC)CC)C.[S:8](Cl)([CH3:11])(=[O:10])=[O:9].[OH:13][CH:14]1[CH2:17][C:16]2([CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18]2)[CH2:15]1>ClCCl>[CH3:11][S:8]([O:13][CH:14]1[CH2:15][C:16]2([CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18]2)[CH2:17]1)(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 69669842tert-Butyl 2-hydroxy-6-azaspiro(3.4)octane-6-carboxylate

Product 1

HCID 86660639tert-Butyl 2-[(methylsulfonyl)oxy]-6-azaspiro[3.4]octane-6-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.76 mL (5.49 mmol) of triethylamine and then 0.43 mL (5.49 mmol) of mesyl chloride are added to a solution of 1.52 g (4.99 mmol) of tert-butyl 2-hydroxy-6-azaspiro[3.4]octane-6-carboxylate, obtained in step 6.1., in 45 mL of dichloromethane. The reaction medium is stirred at room temperature for 1 hour 30 minutes. After evaporating off the solvent, water is added to the reaction medium, the aqueous phase is separated out and extracted several times with dichloromethane, the combined organic phases are washed with saturated aqueous sodium chloride solution and dried over sodium sulfate, and the filtrate is concentrated under reduced pressure. After evaporating off the solvent, 1.90 g of product are obtained in the form of a brown oil, which is used without further purification in the following step.

Workup

  1. customobtained in step 6.1
  2. customAfter evaporating off the solvent, water
  3. additionis added to the reaction medium
  4. customthe aqueous phase is separated out
  5. extractionextracted several times with dichloromethane
  6. washthe combined organic phases are washed with saturated aqueous sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. concentrationthe filtrate is concentrated under reduced pressure
  9. customAfter evaporating off the solvent, 1.90 g of product
  10. customare obtained in the form of a brown oil, which
  11. customis used without further purification in the following step

Sources & evidence

ORD record
ord-6cbe3ba914b1450e87436a480e16a9a4
Source dataset
uspto-grants-2014_11
Patent number
US08889702B2

Reaction notes

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