4-Nitrobenzyl chloroformate → HCID 13137268, compound

HRID 1723827Notes

Reaction equation

HRID 1723827 reaction equation
[NH:1]1[CH2:5][CH2:4][CH:3]([OH:6])[CH2:2]1.Cl[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1)=[O:9]>O1CCOCC1.O.O1CCOCC1>[OH:6][CH:3]1[CH2:4][CH2:5][N:1]([C:8]([O:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][CH:17]=2)=[O:9])[CH2:2]1

Participants

5

Reactant 2

HCID 782054-Nitrobenzyl chloroformateHCID 982104-Hydroxypyrrolidine

Product 1

HCID 13137268HCID 13137268, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
5 °C

Procedure

A solution of 3-pyrrolidinol (4.0 g) in dioxane-water (10:1, 50 ml) mixed solvent was cooled to 5° C., and into which a solution of 4-nitrobenzyl chloroformate (10.9 g) in dioxane (20 ml) was added dropwise, while maintaining the pH at 8-9, followed by 10 minutes' stirring at 5° C. Distilling the solvent off under reduced pressure, the residue was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and from which the solvent was distilled off under reduced pressure. Washing the residue with ethyl acetate, 3-hydroxy-1-(p-nitrobenzyloxycarbonyl)pyrrolidine (6.6 g) was obtained as a pale yellow solid.

Workup

  1. temperaturewhile maintaining the pH at 8-9
  2. distillationDistilling the solvent off under reduced pressure
  3. extractionthe residue was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. distillationfrom which the solvent was distilled off under reduced pressure
  6. washWashing the residue with ethyl acetate

Sources & evidence

ORD record
ord-d9ecb31b3afa4325a23002c9ff50fc66
Source dataset
uspto-grants-2009_02
Patent number
US07485647B2

Reaction notes

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