4-Toluenesulfonyl chloride → 4-Fluoro-1-(toluene-4-sulfonyl)-piperidine-4-carboxylic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1([F:12])[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1>N1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1([F:12])[CH2:7][CH2:8][N:9]([S:19]([C:16]2[CH:17]=[CH:18][C:13]([CH3:23])=[CH:14][CH:15]=2)(=[O:21])=[O:20])[CH2:10][CH2:11]1)=[O:5])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
4-Fluoro-piperidine-4-carboxylic acid ethyl ester (1.263 g), synthesis described in patent application US2004/10013, was dissolved in pyridine (70 ml) and p-toluenesulfonyl chloride (1.512 g) was added and the mixture was stirred at RT for 48 h under an argon atmosphere. Then the solvent was evaporated off, the residue partitioned between AcOEt and aqueous HCl, the organic layer was separated, washed with brine, dried over sodium sulphate and concentratedin vacuo to give a brown oil which was purified by flash chromatography (AcOEt/Heptane, gradient from 0 to 25%) to give the desired 4-fluoro-1-(toluene-4-sulfonyl)-piperidine-4-carboxylic acid ethyl ester (2.086 g) as a white solid. MS (ESI): 330.0 (MH+).
Workup
- customThen the solvent was evaporated off
- customthe residue partitioned between AcOEt and aqueous HCl
- customthe organic layer was separated
- washwashed with brine
- dry with materialdried over sodium sulphate and concentratedin vacuo
- customto give a brown oil which
- customwas purified by flash chromatography (AcOEt/Heptane, gradient from 0 to 25%)
Sources & evidence
- ORD record
- ord-a7a1bdfc222b4d5b95efebf4ef37614a
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08258158B2
Reaction notes
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