Dimethyl Sulfoxide → (+/-)-trans-3-[2-(2-Chloro-phenyl)-5,7-dimethoxy-4-oxo-4h-chromen-8-yl]-1-methyl-pyrrolidine-2-carbaldehyde

HRID 1363398Notes

Reaction equation

HRID 1363398 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1[O:19][C:20]2[C:25]([C:26](=[O:28])[CH:27]=1)=[C:24]([O:29][CH3:30])[CH:23]=[C:22]([O:31][CH3:32])[C:21]=2[C@@H:33]1[CH2:37][CH2:36][N:35]([CH3:38])[C@H:34]1[CH2:39][OH:40].C([O-])(O)=O.[Na+]>C(Cl)Cl.C(N(CC)CC)C>[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1[O:19][C:20]2[C:25]([C:26](=[O:28])[CH:27]=1)=[C:24]([O:29][CH3:30])[CH:23]=[C:22]([O:31][CH3:32])[C:21]=2[C@@H:33]1[CH2:37][CH2:36][N:35]([CH3:38])[C@H:34]1[CH:39]=[O:40]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 59318486(+)-trans-2-(2-Chloro-phenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one

Product 1

HCID 131728687(+/-)-trans-3-[2-(2-Chloro-phenyl)-5,7-dimethoxy-4-oxo-4h-chromen-8-yl]-1-methyl-pyrrolidine-2-carbaldehyde

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolvent

Procedure

Dimethyl sulfoxide (1.8 mL, 25.3 mmol) in methylene chloride (20 mL) was added to a stirred solution of oxalyl chloride (840 μL, 9.84 mmol) in dry methylene chloride (120 mL) dropwise at −50° C. The reaction mixture was stirred for 30 min. Compound of example 7, (2.0 g, 4.65 mmol) in methylene chloride (20 mL) was added dropwise to the reaction mixture. The resulting mixture was further stirred for 30 min. Triethylamine was added dropwise at −50° C. and the reaction mixture was warmed to room temperature and basified with NaHCO3 solution (10 mL). Reaction mixture was extracted with methylene chloride, organic layer was washed with water, brine and dried (anhydrous Na2SO4) to afford the title compound.

Workup

  1. stirringThe resulting mixture was further stirred for 30 min
  2. customReaction mixture
  3. extractionwas extracted with methylene chloride, organic layer
  4. washwas washed with water, brine
  5. dry with materialdried (anhydrous Na2SO4)

Sources & evidence

ORD record
ord-907217e9d3e94e3d9c3f82c77110a939
Source dataset
uspto-grants-2011_02
Patent number
US07884127B2

Reaction notes

Loading…