Diisopropylethylamine → cis Ethyl 1-ethoxycarbonyl-3-[2-(benzyloxymethoxy)ethyl]-pyrrolidine-2-carboxylate

HRID 1164890Notes

Reaction equation

HRID 1164890 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:10][CH2:9][C@H:8]([CH2:11][CH2:12][OH:13])[C@@H:7]1[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:5])[CH3:2].C(N(C(C)C)CC)(C)C.[CH2:28]([O:35][CH2:36]Cl)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(Cl)Cl>[CH2:1]([O:3][C:4]([N:6]1[CH2:10][CH2:9][C@H:8]([CH2:11][CH2:12][O:13][CH2:36][O:35][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C@@H:7]1[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 137983Benzyl chloromethyl etherHCID 86743786cis 1-Ethoxycarbonyl-2-ethoxycarbonylpyrrolidine-3-ethanol

Product 1

HCID 131716329cis Ethyl 1-ethoxycarbonyl-3-[2-(benzyloxymethoxy)ethyl]-pyrrolidine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6 g of cis 1-ethoxycarbonyl-2-ethoxycarbonylpyrrolidine-3-ethanol in 75 ml of methylene chloride containing 7.3 ml of diisopropylethylamine, to which is added 5.1 ml of 85% benzyloxymethyl chloride, is stirred 31/2 hours at room temperature. The solution is washed with water and saturated aqueous sodium bicarbonate. The solution is then dried over sodium sulfate, filtered, concentrated and purified by flash chromatography using ethyl acetate/hexane (1:4) to yield cis ethyl 1-ethoxycarbonyl-3-[2-(benzyloxymethoxy)-ethyl]-pyrrolidine-2-carboxylate.

Workup

  1. washThe solution is washed with water and saturated aqueous sodium bicarbonate
  2. dry with materialThe solution is then dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by flash chromatography

Sources & evidence

ORD record
ord-eda91b4bdc8c401f91b46af9e99c00f4
Source dataset
uspto-grants-1990_03
Patent number
US04906621

Reaction notes

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