Hydrochloric Acid → HCID 57206111, compound

HRID 1954086Notes

Reaction equation

HRID 1954086 reaction equation
[OH:1][C@H:2]1[CH2:6][CH2:5][NH:4][CH2:3]1.C(N(CC)CC)C.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.Cl>O1CCOCC1.O>[OH:1][C@H:2]1[CH2:6][CH2:5][N:4]([S:22]([C:19]2[CH:18]=[CH:17][C:16]([O:15][CH3:14])=[CH:21][CH:20]=2)(=[O:24])=[O:23])[CH2:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 2733874(3S)-pyrrolidin-3-ol

Product 1

HCID 57206111HCID 57206111, compoundYield 88.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

The 3(S)-hydroxy-pyrrolidine (1.0 g, 11.5 mmol), triethylamine (2.32 g, 22.9 mmol, 2.0 equiv) in 1,4-dioxane (30 mL) and water (10 mL) is stirred at room temperature and then 4-methoxyphenylsulfonyl chloride (2.61 g, 12.6 mmol, 1.10 equiv) is added. The resulting solution is stirred at room temperature for 3 h. and then the solution is acidified to pH~1 with 1 N HCl. The solution is poured into water and then extracted with CH2Cl2. The organic extracts are dried (Na2SO4) and concentrated o an oil. The oil is purified by chromatography using 1/1 hexane/EtOAc as the eluent to afford 2.62 g (81%) of the desired product as a colorless oil.

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe organic extracts are dried (Na2SO4)
  3. concentrationconcentrated o an oil
  4. customThe oil is purified by chromatography

Sources & evidence

ORD record
ord-69a97ab895034ee794091d101474f5ab
Source dataset
uspto-grants-2000_09
Patent number
US06121272

Reaction notes

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