Water → Benzyl 3-hydroxypyrrolidine-1-carboxylate

HRID 1755674Notes

Reaction equation

HRID 1755674 reaction equation
[NH:1]1[CH2:5][CH2:4][CH:3]([OH:6])[CH2:2]1.C(N(CC)CC)C.[CH2:14]([O:21][C:22](Cl)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>C(Cl)(Cl)Cl>[CH2:14]([O:21][C:22]([N:1]1[CH2:5][CH2:4][CH:3]([OH:6])[CH2:2]1)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 982104-Hydroxypyrrolidine

Product 1

HCID 560953Benzyl 3-hydroxypyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

30 mg of 3-pyrrolidinol was dissolved in 500 ml of chloroform, to which 53 mg of triethylamine was added, followed by gradually dropping 52 ml of benzyloxycarbonyl chloride at room temperature. After completion of the reaction, the reaction solution was poured into water and extracted with chloroform. The solvent was distilled off under reduced pressure and the resultant residue was purified by column chromatography (eluting solvent: hexane-ethyl acetate) to obtain 70.67 g of the intended compound.

Workup

  1. additionwas added
  2. customat room temperature
  3. customAfter completion of the reaction
  4. extractionextracted with chloroform
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe resultant residue was purified by column chromatography (eluting solvent: hexane-ethyl acetate)

Sources & evidence

ORD record
ord-a451a0e619074d368db5bcb8b9606907
Source dataset
uspto-grants-1995_08
Patent number
US05438045

Reaction notes

Loading…