Triethylamine → 1,3-Dibenzyl-8-methanesulfonyl-1,4,8-triazaspiro[4,5]decan-2-one

HRID 227256Notes

Reaction equation

HRID 227256 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[CH2:13]([N:20]1[C:24]2([CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[NH:23][CH:22]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:21]1=[O:37])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[CH2:13]([N:20]1[C:24]2([CH2:25][CH2:26][N:27]([S:9]([CH3:8])(=[O:11])=[O:10])[CH2:28][CH2:29]2)[NH:23][CH:22]([CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:21]1=[O:37])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 31297Methanesulfonyl chlorideHCID 688379421,3-Dibenzyl-1,4,8-triazaspiro[4,5]decan-2-one

Product 1

HCID 688377601,3-Dibenzyl-8-methanesulfonyl-1,4,8-triazaspiro[4,5]decan-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.15 ml, 1.78 mmol) and subsequently methanesulfonyl chloride (0.14 ml, 1.78 mmol) were added to a solution of 1,3-dibenzyl-1,4,8-triazaspiro-[4,5]decan-2-one (300 mg, 0.89 mmol) in CH2Cl2 (8.1 ml) with stirring using nitrogen as an inert gas at RT. The reaction mixture was stirred overnight. The organic phase was rendered alkaline using aqueous sodium carbonate solution (20 ml) and the aqueous phase was extracted with CH2Cl2 (15 ml). The combined organic phases were dried over Na2SO4. After filtration, removal of the solvent, and column chromatography, the desired product 1,3-dibenzyl-8-methanesulfonyl-1,4,8-triazaspiro[4,5]decan-2-one was obtained in a yield of 287 mg (77% of theory).

Workup

  1. customat RT
  2. stirringThe reaction mixture was stirred overnight
  3. extractionthe aqueous phase was extracted with CH2Cl2 (15 ml)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. filtrationAfter filtration, removal of the solvent, and column chromatography

Sources & evidence

ORD record
ord-7c42931adaa44c64920a7af1ef5adef0
Source dataset
uspto-grants-2009_07
Patent number
US07560468B2

Reaction notes

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