Hydrochloric Acid → HCID 57234713, compound

HRID 1954087Notes

Reaction equation

HRID 1954087 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:7][CH2:6][NH:5][CH2:4]1.C(N(CC)CC)C.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.Cl>O1CCOCC1.O>[OH:1][CH2:2][C@H:3]1[CH2:7][CH2:6][N:5]([S:23]([C:20]2[CH:19]=[CH:18][C:17]([O:16][CH3:15])=[CH:22][CH:21]=2)(=[O:25])=[O:24])[CH2:4]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 7446911(3S)-3-Pyrrolidinemethanol

Product 1

HCID 57234713HCID 57234713, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

The 3(S)-hydroxymethylpyrrolidine (0.9 g, 8.90 mmol), triethylamine (1.80 g, 17.8 mmol, 2.0 equiv) in 1,4-dioxane (30 mL) and water (10 mL) is stirred at room temperature and then 4-methoxyphenylsulfonyl chloride (2.02 g, 9.80 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 to an oil. The oil is purified by chromatography using 1/1 hexane/EtOAc as the eluent to afford the desired product as a colorless oil.

Workup

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

Sources & evidence

ORD record
ord-5a87f8ab595b4b8a8db5c396bc1dc5fc
Source dataset
uspto-grants-2000_09
Patent number
US06121272

Reaction notes

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