Water → 2-((R)-1-ethylpyrrolidin-3-ylmethyl)-4-fluorobenzenesulfonyl chloride

HRID 927980Notes

Reaction equation

HRID 927980 reaction equation
[CH2:1]([N:3]1[CH2:7][CH2:6][C@@H:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=2)[CH2:4]1)[CH3:2].[Cl:16][S:17](O)(=[O:19])=[O:18].O>ClCCCl>[CH2:1]([N:3]1[CH2:7][CH2:6][C@@H:5]([CH2:8][C:9]2[CH:10]=[C:11]([F:15])[CH:12]=[CH:13][C:14]=2[S:17]([Cl:16])(=[O:19])=[O:18])[CH2:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 24638Chlorosulfonic acidHCID 70983712(R)-1-ethyl-3-(3-fluorobenzyl)pyrrolidine2×

Product 1

HCID 867133192-((R)-1-ethylpyrrolidin-3-ylmethyl)-4-fluorobenzenesulfonyl chloride

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of (R)-1-ethyl-3-(3-fluorobenzyl)pyrrolidine (Intermediate 97, 0.24 g) in DCE (1.2 mL) was added carefully to chlorosulfonic acid and the mixture was stirred at room temperature for 2 hours. The mixture was carefully poured into iced water and extracted with DCM, dried (MgSO4) and filtered. The filtrate was evaporated to dryness to give 2-((R)-1-ethyl-pyrrolidin-3-ylmethyl)-4-fluorobenzenesulfonyl chloride (0.36 g) as an oil which was used without further charactersiation.

Workup

  1. extractionextracted with DCM
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-62ef2b1292f04974954549b2f8f61d4d
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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