Methanesulfonyl chloride → HCID 24728873, compound

HRID 1723696Notes

Reaction equation

HRID 1723696 reaction equation
[CH2:1]([N:8]1[CH2:12][C@@H:11]([OH:13])[C@H:10]([OH:14])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>ClCCl>[CH2:1]([N:8]1[CH2:12][C@@H:11]([O:13][S:16]([CH3:15])(=[O:18])=[O:17])[C@H:10]([O:14][S:16]([CH3:15])(=[O:18])=[O:17])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 7021491(3R,4R)-1-Benzylpyrrolidine-3,4-diol

Product 1

HCID 24728873HCID 24728873, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cold (0-5° C.) solution of the product from Step 2 (5.27 g, 27.3 mmol) and TEA (8.27 g, 81.9 mmol) in dichloromethane (50 mL), was added methanesulfonyl chloride (6.87 g, 60.0 mmol) over a period of 30 minutes. After stirring at RT overnight, the reaction mixture was washed with water. The organic layer was dried (sodium sulfate), filtered, and concentrated to give the crude product which was purified over a silica column (5:95 EtOAc/hexane) to obtain pure product (6.44 g, 67.6%). 1H NMR (400 MHz, CDCl3) δ 7.32-7.26 (5H, m), 5.14 (2H, m), 3.65 (2H, s), 3.15-3.08 (2H, m), 3.08 (6H, s), 2.76 (2H, dd). MS m/z 350 (MH+).

Workup

  1. washthe reaction mixture was washed with water
  2. dry with materialThe organic layer was dried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give the crude product which
  6. customwas purified over a silica column (5:95 EtOAc/hexane)

Sources & evidence

ORD record
ord-329f4c7d8f664b418841d0481141ec67
Source dataset
uspto-grants-2009_02
Patent number
US07485641B2

Reaction notes

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