Dimethyl Sulfoxide → HCID 15671519, compound

HRID 1088280Notes

Reaction equation

HRID 1088280 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([O:18][C:19]([N:21]1[CH2:25][C@H:24]([O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[CH2:23][C@H:22]1[CH2:34][CH2:35][CH2:36][OH:37])=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl>[CH2:11]([O:18][C:19]([N:21]1[CH2:25][C@H:24]([O:26][Si:27]([C:30]([CH3:31])([CH3:32])[CH3:33])([CH3:29])[CH3:28])[CH2:23][C@H:22]1[CH2:34][CH2:35][CH:36]=[O:37])=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 15671483HCID 15671483, compound

Product 1

HCID 15671519HCID 15671519, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride (0.32 ml) was dissolved in 7.9 ml of dry dichloromethane, and 0.56 ml of dry dimethylsulfoxide was added thereto at -45° to -56° C. in a nitrogen stream, followed by stirring at the same temperature for 20 minutes. To the reaction mixture was added a solution of 1.30 g of (2R,4R)-1-benzyloxycarbonyl-2-(3-hydroxypropyl)-4-t-butyldimethylsilyloxypyrrolidine in 6.2 ml of dry dichloromethane at -50° to -60° C., followed by stirring at the same temparature for 15 minutes. Then, 2.2 ml of triethylamine was added thereto at -50° to -60° C. The temparature was elevated to room temperature, and the reaction mixture was washed successively with brine, dilute hydrochloric acid and brine, dried over anhydrous sodium sulfate and distilled to obtain (2R,4R)-1-benzyloxycarbonyl-2-(2-formylethyl)-4-t-butyldimethylsilyloxypyrrolidine.

Workup

  1. customat -45° to -56° C.
  2. stirringby stirring at the same temparature for 15 minutes
  3. customat -50° to -60° C
  4. customwas elevated to room temperature
  5. washthe reaction mixture was washed successively with brine, dilute hydrochloric acid and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationdistilled

Sources & evidence

ORD record
ord-92219e2baf2d4962a73a0c6921bca0ed
Source dataset
uspto-grants-1990_10
Patent number
US04962103

Reaction notes

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