4-Toluenesulfonyl chloride → HCID 9905116, compound

HRID 1594690Notes

Reaction equation

HRID 1594690 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:12][CH2:11][CH2:10][NH:9]2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:12][CH2:11][CH2:10][N:9]2[S:26]([C:23]2[CH:24]=[CH:25][C:20]([CH3:30])=[CH:21][CH:22]=2)(=[O:28])=[O:27])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 39124022-(3-Fluorophenyl)pyrrolidine

Product 1

HCID 9905116HCID 9905116, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (RS)-2-(3-fluoro-phenyl)-pyrrolidine (0.24 g, 1.45 mmol) and triethylamine (0.40 ml, 2.87 mmol) in dichloromethane (40 ml) was added at 0° C. toluene-4-sulfonyl chloride (0.42 g, 2.20 mmol). The mixture was stirred at RT for 16 h, evaporated, dissolved in water (40 ml) and extracted with ethyl acetate (2×40 ml). The combined organic layers were washed with water (40 ml), brine (40 ml), dried (MgSO4) and evaporated. The crude product was purified by crystallization from ethyl acetate/hexane to give the product (0.38 g, 83%) as a white solid, m.p. 116° C. and MS: m/e=319 (M+).

Workup

  1. customevaporated
  2. dissolutiondissolved in water (40 ml)
  3. extractionextracted with ethyl acetate (2×40 ml)
  4. washThe combined organic layers were washed with water (40 ml), brine (40 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe crude product was purified by crystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-009524c187aa4f058953c3f61abf70a5
Source dataset
uspto-grants-2001_09
Patent number
US06284785B1

Reaction notes

Loading…