Methanol → 8-(2-Chloro-benzenesulfonyl)-2,8-diaza-spiro[4.5]decan-1-one

HRID 2194130Notes

Reaction equation

HRID 2194130 reaction equation
C([O:3][C:4]([C:6]1([CH2:22][CH2:23][NH2:24])[CH2:11][CH2:10][N:9]([S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:21])(=[O:14])=[O:13])[CH2:8][CH2:7]1)=O)C.[Cl-].C[Al+]C.CO>C1(C)C=CC=CC=1.CCCCCCC>[Cl:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[S:12]([N:9]1[CH2:10][CH2:11][C:6]2([C:4](=[O:3])[NH:24][CH2:23][CH2:22]2)[CH2:7][CH2:8]1)(=[O:13])=[O:14]

Participants

6

Reactant 3

HCID 887MethanolHCID 16686359Dimethylalumanylium chlorideHCID 595780964-(2-Amino-ethyl)-1-(2-chloro-benzenesulfonyl)-piperidine-4-carboxylic acid ethyl ester

Product 1

HCID 595779948-(2-Chloro-benzenesulfonyl)-2,8-diaza-spiro[4.5]decan-1-oneYield 72.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8900HeptaneSolvent

Procedure

4-(2-Amino-ethyl)-1-(2-chloro-benzenesulfonyl)-piperidine-4-carboxylic acid ethyl ester (7.09 g) was suspended in toluene under an argon atmosphere, dimethylaluminium chloride in heptane (1 molar, 28.39 ml) was added and the mixture was stirred 5 minutes at RT then refluxed for 3 hours. It was then was cooled to RT, MeOH (40 ml) was added and the mixture was stirred for 30 minutes. The solvent was removed, the residue was adsorbed on silica gel and purified by flash chromatography over silica gel (eluents: AcOEt/CH2Cl2 5 to 50% then acetone/CH2Cl2 10 to 30%) to give the desired material (4.5 g) as light yellow solid. MS (ESI): 329.0 (MH+).

Workup

  1. temperaturethen refluxed for 3 hours
  2. temperatureIt was then was cooled to RT
  3. stirringthe mixture was stirred for 30 minutes
  4. customThe solvent was removed
  5. custompurified by flash chromatography over silica gel (eluents

Sources & evidence

ORD record
ord-9eb897055eba4ae99dd2db8cf550b625
Source dataset
uspto-grants-2012_12
Patent number
US08329904B2

Reaction notes

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