Thionyl Chloride → HCID 23000719, compound

HRID 397676Notes

Reaction equation

HRID 397676 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([O:12][C:13]([N:15]1[CH2:19][CH2:18][CH:17]([CH2:20][S:21]([OH:24])(=O)=[O:22])[CH2:16]1)=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CN(C)C=O>[Cl:3][S:21]([CH2:20][CH:17]1[CH2:18][CH2:19][N:15]([C:13]([O:12][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:14])[CH2:16]1)(=[O:24])=[O:22]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 54463658HCID 54463658, compound

Product 1

HCID 23000719HCID 23000719, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Thionyl chloride (5 ml) was added to a solution of 1-[(benzyloxy)carbonyl]-3-pyrrolidinylmethanesulfonic acid (600 mg) [Preparation 57] in dimethylformamide (50 ml). The reaction mixture was heated to reflux for 20 mins after which time the cooled mixture was evaporated to dryness. The residue was partitioned between ethyl acetate and water. The organic layer was separated, dried over magnesium sulphate and the solvent removed under reduced pressure to afford benzyl 3-(chlorosulfonylmethyl)-1-pyrrolidinecarboxylate (560 mg) as an oil.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 20 mins after which time the cooled mixture
  3. customwas evaporated to dryness
  4. customThe residue was partitioned between ethyl acetate and water
  5. customThe organic layer was separated
  6. dry with materialdried over magnesium sulphate
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-e6b8ccbbbfcf419990e256a8cad28cb2
Source dataset
uspto-grants-2003_08
Patent number
US06610707B1

Reaction notes

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