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

HRID 345356Notes

Reaction equation

HRID 345356 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-b575bb89198a4c04a72a7a55b45b5098
Source dataset
uspto-grants-1991_10
Patent number
US05057506

Reaction notes

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