Methanesulfonyl chloride → HCID 69427827, compound

HRID 1006845Notes

Reaction equation

HRID 1006845 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@@H:8]([C:11]([O:13][CH3:14])=[O:12])[CH2:7][NH:6]1)=[O:4].[CH3:15][S:16](Cl)(=[O:18])=[O:17]>ClCCl.CN(C)C1C=CN=CC=1>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH:8]([C:11]([O:13][CH3:14])=[O:12])[CH2:7][N:6]1[S:16]([CH3:15])(=[O:18])=[O:17])=[O:4]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 13413095HCID 13413095, compound

Product 1

HCID 69427827HCID 69427827, compoundYield 93.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

6-ring: To rac-cis-Piperidine-2,5-dicarboxylic acid dimethyl ester [Frank J., J. Heterocyclic Chem. 32, 857-861 (1995)] (36.2 g) dissolved in dichloromethane (720 ml) were added 4-dimethylaminopyridine (33.0 g) and, dropwise, methanesulphonyl chloride (28.6 g) within 10 minutes and room temperature. The temperature rose to 35° C. The reaction mixture was stirred 1 h at room temperature, washed with 2 molar HCJ, sodium carbonate-solution and brine, dried over magnesium sulphate and concentrated to dryness to obtain (2RS,5RS)-1-methanesulfonyl-piperidine-2,5-dicarboxylic acid dimethyl ester (46.8 g) as a syrup, MS: 220 (M+-59).

Workup

  1. customroom temperature
  2. customrose to 35° C
  3. washwashed with 2 molar HCJ, sodium carbonate-solution and brine
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-5118bca53620470d94d533d239e4f52d
Source dataset
uspto-grants-2004_09
Patent number
US06790860B2

Reaction notes

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