Hydrochloric Acid → Methyl 2-(1-(3,4-dichlorophenylsulfonyl)pyrrolidin-2-yl)acetate

HRID 1642143Notes

Reaction equation

HRID 1642143 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9](Cl)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:13][O:14][C:15](=[O:22])[CH2:16][CH:17]1[CH2:21][CH2:20][CH2:19][NH:18]1.Cl>C(Cl)Cl.C(N(CC)CC)C>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:18]2[CH2:19][CH2:20][CH2:21][CH:17]2[CH2:16][C:15]([O:14][CH3:13])=[O:22])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7383Benzenesulfonyl chloride, 3,4-dichloro-HCID 5323862Methyl 2-(pyrrolidin-2-yl)acetate

Product 1

HCID 66756029Methyl 2-(1-(3,4-dichlorophenylsulfonyl)pyrrolidin-2-yl)acetate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

A solution of 3,4-dichlorobenzenesulfonyl chloride (1.88 g, 7.65 mmol) in DCM (15 ml) was added dropwise at 0° C. to a solution, cooled to 0° C., of pyrrolidin-2-ylacetic acid methyl ester (1.5 g, 8.4 mmol) in DCM (33 ml) and triethylamine was (2.66 ml, 21 mmol), and stirring was then carried out for 90 minutes at room temperature. 0.5 M HCl (20 ml) was then added, and stirring was carried out for a further 15 minutes. The organic phase was separated, washed with water and dried over sodium sulfate. The solvent was removed using a rotary evaporator and the product was used in the next stage without being purified further. Yield: 2.1 g (77%)

Workup

  1. stirringstirring
  2. waitwas carried out for a further 15 minutes
  3. customThe organic phase was separated
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was removed
  7. customa rotary evaporator
  8. customwithout being purified further

Sources & evidence

ORD record
ord-afc8ef7011c644f5a030ab3b2fe811ff
Source dataset
uspto-grants-2012_02
Patent number
US08119633B2

Reaction notes

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