Dimethyl Sulfoxide → tert-butyl (2S)-2-formylpyrrolidine-1-carboxylate

HRID 2199333Notes

Reaction equation

HRID 2199333 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH2:12][C@@H:13]1[CH2:17][CH2:16][CH2:15][N:14]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].C(N(CC)CC)C>ClCCl>[CH:12]([C@@H:13]1[CH2:17][CH2:16][CH2:15][N:14]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:11]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 643448(S)-(-)-N-Boc-prolinol

Product 1

HCID 2734674tert-butyl (2S)-2-formylpyrrolidine-1-carboxylateYield 55.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Oxalyl chloride (3.2 mL, 0.04 mol) and dimethyl sulfoxide (4.3 mL, 0.06 mol) were dissolved in 100 mL of dichloromethane in a dry ice bath. After stirring for 30 minutes, a solution of tert-butyl (2S)-2-(hydroxymethyl)pyrrolidine-1-carboxylate 2b (2 g, 0.01 mol) in 20 mL of dichloromethane was added dropwise. The reaction mixture was stirred for 45 minutes, and triethylamine (7.08 g, 0.07 mol) was added dropwise. After stirring for another 1 hours at 0° C., the reaction mixture was added with 500 mL of dichloromethane. The combined organic layers were washed with saturated brine (100 mL×2), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography with elution system A to obtain the title compound tert-butyl(2S)-2-formylpyrrolidine-1-carboxylate 2c (1.10 g, yield 55.4%) as a light yellow oil.

Workup

  1. stirringThe reaction mixture was stirred for 45 minutes
  2. stirringAfter stirring for another 1 hours at 0° C.
  3. washThe combined organic layers were washed with saturated brine (100 mL×2)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography with elution system

Sources & evidence

ORD record
ord-31cedd6d6c0640ad8c8bc56cde15fe15
Source dataset
uspto-grants-2016_06
Patent number
US09358227B2

Reaction notes

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