Dimethyl Sulfoxide → HCID 20802795, compound

HRID 1195659Notes

Reaction equation

HRID 1195659 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[N+:11]([C:14]1[CH:38]=[CH:37][C:17]([CH2:18][O:19][C:20]([N:22]2[CH2:26][CH:25]([O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[CH2:24][CH:23]2[CH2:35][OH:36])=[O:21])=[CH:16][CH:15]=1)([O-:13])=[O:12].CCN(CC)CC>C(Cl)Cl>[O:27]([C@H:25]1[CH2:26][N:22]([C:20]([O:19][CH2:18][C:17]2[CH:16]=[CH:15][C:14]([N+:11]([O-:13])=[O:12])=[CH:38][CH:37]=2)=[O:21])[C@H:23]([CH:35]=[O:36])[CH2:24]1)[Si:28]([C:31]([CH3:34])([CH3:32])[CH3:33])([CH3:30])[CH3:29]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 15622381HCID 15622381, compound

Product 1

HCID 20802795HCID 20802795, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred mixture of molecular sieves dried DMSO (15.0 ml, 212 mmol) and dichloromethane (1.24l ) at -78° C. was added oxalyl chloride (10.0 ml, 114 mmol) dropwise over 5 minutes and stirring was continued for additional 10 minutes. To this solution was added a mixture of 1-(4-nitrobenzyloxycarbonyl) -2-hydroxymethyl-4-(tertbutyldimethylsiloxy) pyrrolidine (31.0 g, 75.6 mmol) and CH2Cl2 (155 ml) dropwise over 15 minutes and the stirring was continued for 30 minutes at the same temperature. After addition of Et3N (52.5 ml, 377 mmol), removing of cold bath to warm to room temperature, washed with aqueous saturated NaHCO3 (300 ml), dried (MgSO4) of organic portion and concentrated in vacuo to afford the oily product which became solid after storage at room temperature. This crystalline product was washed with diethyl ether-hexane (1:10), collected by filtration and dried to give (2S, 4R)-4-tert-butyl-dimethylsiloxy-2-formyl-N-(4-nitrobenzyloxycarbonyl)pyrrolidine (29.7 g, 96% yield).

Workup

  1. additionTo this solution was added
  2. waitthe stirring was continued for 30 minutes at the same temperature
  3. customremoving of cold bath
  4. washwashed with aqueous saturated NaHCO3 (300 ml)
  5. dry with materialdried (MgSO4) of organic portion
  6. concentrationconcentrated in vacuo
  7. customto afford the oily product which
  8. customat room temperature
  9. washThis crystalline product was washed with diethyl ether-hexane (1:10)
  10. filtrationcollected by filtration
  11. customdried

Sources & evidence

ORD record
ord-aff9d66f1304468a9fec6807f425468c
Source dataset
uspto-grants-1992_05
Patent number
US05112818

Reaction notes

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