Dimethyl Sulfoxide → (2S,4R)-1-allyloxycarbonyl-4-t-butyldimethylsilyloxy-2-formylpyrrolidine

HRID 975630Notes

Reaction equation

HRID 975630 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([O:14][C:15]([N:17]1[CH2:21][C@H:20]([O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[CH2:19][C@H:18]1[CH2:30][OH:31])=[O:16])[CH:12]=[CH2:13].C(N(CC)CC)C>ClCCl>[CH2:11]([O:14][C:15]([N:17]1[CH2:21][C@H:20]([O:22][Si:23]([C:26]([CH3:28])([CH3:27])[CH3:29])([CH3:24])[CH3:25])[CH2:19][C@H:18]1[CH:30]=[O:31])=[O:16])[CH:12]=[CH2:13]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 15537957HCID 15537957, compound

Product 1

HCID 22870383(2S,4R)-1-allyloxycarbonyl-4-t-butyldimethylsilyloxy-2-formylpyrrolidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of oxalyl chloride (2.53 ml) and dichloromethane (90 ml) was dropwise added dimethyl sulfoxide (4.31 ml) at -40° C.~-50° C. with stirring and the mixture was stirred at the same temperature for 5 minutes. To the solution was added dropwise a solution of (2S,4R)-1-allyloxycarbonyl-4-t-butyldimethylsiloxy-2-(hydroxymethyl)pyrrolidine (8.70 g) in dichloromethane (45 ml) at -40° C.~-50° C. After 10 minutes with stirring, triethylamine (19.2 ml) was dropwise added to the solution and the mixture was stirred at 0°~10° C. for 30 minutes. The insoluble material was filtered off and the filtrate was washed successively with 1N hydrochloric acid, water, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated in vacuo to give a residue of (2S,4R)-1-allyloxycarbonyl-4-t-butyldimethylsiloxy-2-formylpyrrolidine.

Workup

  1. customat -40° C.~-50° C.
  2. stirringthe mixture was stirred at the same temperature for 5 minutes
  3. stirringAfter 10 minutes with stirring
  4. stirringthe mixture was stirred at 0°~10° C. for 30 minutes
  5. filtrationThe insoluble material was filtered off
  6. washthe filtrate was washed successively with 1N hydrochloric acid, water, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-4d9df517e9da4590913e9d66880c5eba
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

Loading…