Triethylamine → HCID 66854958, compound

HRID 1970569Notes

Reaction equation

HRID 1970569 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13](=[O:19])[CH2:14][C:15](=[N:17]O)[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(Cl)(=O)=O.C(N(CC)CC)C>ClCCl>[CH2:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]1[O:19][N:17]=[C:15]([CH3:16])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86650481HCID 86650481, compound

Product 1

HCID 66854958HCID 66854958, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 878 mg 1-((S)-1-Benzyl-pyrrolidin-2-yl)-butane-1,3-dione 3-oxime in 50 ml dichloromethane were added 0.52 ml methanesulfonyl chloride and 0.94 ml triethylamine at 0° C. The solution was allowed to warm to RT within 5 h. The reaction mixture was extracted with 1 M HCl (3×), the aqueous extracts were neutralized with solid NaHCO3 and extracted with dichloromethane (3×) to give the crude product which was purified by chromatography on silica using ethyl acetate/heptane 1/2 as eluent.

Workup

  1. extractionThe reaction mixture was extracted with 1 M HCl (3×)
  2. extractionextracted with dichloromethane (3×)

Sources & evidence

ORD record
ord-1fa8077babbb40d8b3af862957c89420
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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