Methanesulfonyl chloride → HCID 12012457, compound

HRID 1804655Notes

Reaction equation

HRID 1804655 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C@H:7]([OH:9])[CH3:8].[CH3:10][S:11](Cl)(=[O:13])=[O:12]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:10][S:11]([O:9][C@@H:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[CH3:8])(=[O:13])=[O:12]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 642847(1R)-1-(Pyridin-2-yl)ethan-1-ol

Product 1

HCID 12012457HCID 12012457, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (1R)-1-pyridin-2-ylethanol (250 mg, 2.03 mmol) and DMAP (496 mg, 4.06 mmol) in DCM (8 mL) was added MsCl (190 μL, 2.44 mmol) at 0° C. The mixture was stirred for 10 min at the same temperature and for an additional hour at RT. The mixture was quenched with ice water and extracted with ethyl acetate (2×15 mL). The organic layer was washed with water and brine, dried over sodium sulfate, filtered, and concentrated under vacuum. The residue oil was purified via prep-plate purification (1000 μM) eluting with 60% ethyl acetate in hexane to afford the product (310 mg, 76%).

Workup

  1. customThe mixture was quenched with ice water
  2. extractionextracted with ethyl acetate (2×15 mL)
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue oil was purified via prep-plate purification (1000 μM)
  8. washeluting with 60% ethyl acetate in hexane

Sources & evidence

ORD record
ord-f6b625cd6cf043c3bd4e11ea308060f9
Source dataset
uspto-grants-2013_01
Patent number
US08354403B2

Reaction notes

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