Triethylamine → 3-Pyrrolidinone benzyl carbamate

HRID 846686Notes

Reaction equation

HRID 846686 reaction equation
[CH2:1]([NH:8][C:9]([O:11][CH:12]1[CH2:16][CH2:15][NH:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C>CS(C)=O>[CH2:1]([NH:8][C:9](=[O:10])[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:14]1[CH2:15][CH2:16][C:12](=[O:11])[CH2:13]1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 216243013-Pyrrolidinol benzyl carbamate

Product 1

HCID 867460623-Pyrrolidinone benzyl carbamate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 31.6 g (0.14 mmol) of 3-pyrrolidinol benzyl carbamate, from Step 1, in 275 mL of DMSO cooled to 0° C. was added 159.25 mL (1.12 mmol) of triethylamine. To this solution, maintained at 0° C. with stirring, was added dropwise over a one hour period a solution of 68.18 g (0.42 mmol) of sulfur trioxide pyridine complex in 250 mL of DMSO. The solution was stirred an additional half-hour at 0° C., then the ice bath was removed and the reaction allowed to proceed for 20 hours at room temperature. The DMSO solution was then poured into 1 L of 20% sodium chloride solution and the product was extracted with three washings of methylene chloride. The methylene chloride solution was washed with 20% NaCl solution to remove excess DMSO, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by evaporation. The dark liquid residue was distilled in a kugelrohr apparatus (140°-160° C. @ 5 Torr) and further purified by chromatography on silica gel (solvent 0.5-2.0% methanol in chloroform) to afford the title compound, MS M/Z 220 (M+H); NMR: d 2.61 (t,2H, J=7.5 Hz), 3.82 (s, 2H), 3.85 (t, 2H, J=7.5 Hz), 5.18 (s, 2H), 7.37 (m, 5H).

Workup

  1. stirringThe solution was stirred an additional half-hour at 0° C.
  2. customthe ice bath was removed
  3. additionThe DMSO solution was then poured into 1 L of 20% sodium chloride solution
  4. extractionthe product was extracted with three washings of methylene chloride
  5. washThe methylene chloride solution was washed with 20% NaCl solution
  6. customto remove excess DMSO
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customthe solvent was removed by evaporation
  10. distillationThe dark liquid residue was distilled in a kugelrohr apparatus (140°-160° C. @ 5 Torr)
  11. customfurther purified by chromatography on silica gel (solvent 0.5-2.0% methanol in chloroform)

Sources & evidence

ORD record
ord-cbf70dcaf17041acb10f89d703cffc77
Source dataset
uspto-grants-1992_08
Patent number
US05137892

Reaction notes

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