Water → Benzyl 3-hydroxypyrrolidine-1-carboxylate

HRID 374809

Reaction equation

HRID 374809 reaction equation
[NH:1]1[CH2:5][CH2:4][CH:3]([OH:6])[CH2:2]1.[CH2:7]([O:14][C:15](Cl)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH2:7]([O:14][C:15]([N:1]1[CH2:5][CH2:4][CH:3]([OH:6])[CH2:2]1)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 962WaterHCID 10387Benzyl chloroformateHCID 982104-Hydroxypyrrolidine

Product 1

HCID 560953Benzyl 3-hydroxypyrrolidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

30 g of 3-pyrrolidinol was dissolved in 500 ml of chloroform, to which 53 ml 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-622ec98462384e448b3f2b77ee2bbe73
Source dataset
uspto-grants-1996_01
Patent number
US05482937

Linked notes

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