Dimethyl Sulfoxide → Benzyl 3-formylpyrrolidine-1-carboxylate

HRID 1501518Notes

Reaction equation

HRID 1501518 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][CH2:12][CH:13]1[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:14]1.O>C(Cl)Cl>[CH:12]([CH:13]1[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:14]1)=[O:11]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 65578Oxalyl chlorideHCID 18332648Benzyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate

Product 1

HCID 4620242Benzyl 3-formylpyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DMSO (597 μL, 8.42 mmol) was added to a solution of oxalyl chloride (427 μL, 5.05 mmol) in DCM (25 mL) at −78° C. After 5 minutes, benzyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate (generated in Step 1) was added. The reaction was continued for 30 minutes at −78° C. TEA (2.3 mL, 17 mmol) was then added. The resulting mixture was then allowed to warm to room temperature over the course of 30 minutes. Water was then added. The layers were separated and the organic phase was washed sequentially with 0.1 N HCl, water, saturated NaHCO3, and brine. The organic phase was then dried over sodium sulfate and the solvent was removed in vacuo to afford the product (0.82 g, 88% over two steps).

Workup

  1. waitThe reaction was continued for 30 minutes at −78° C
  2. customThe layers were separated
  3. washthe organic phase was washed sequentially with 0.1 N HCl, water, saturated NaHCO3, and brine
  4. dry with materialThe organic phase was then dried over sodium sulfate
  5. customthe solvent was removed in vacuo
  6. customto afford the product (0.82 g, 88% over two steps)

Sources & evidence

ORD record
ord-c47786c8f5dc41e88fe1ba518aad9b8b
Source dataset
uspto-grants-2015_12
Patent number
US09206187B2

Reaction notes

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