Iodoethane → (S)-1-(benzyloxycarbonyl)-3-(N,N-diethylamino)pyrrolidine

HRID 13774Notes

Reaction equation

HRID 13774 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:3]1.C(=O)([O-])[O-].[K+].[K+].[CH2:23](I)[CH3:24].O1CC[CH2:28][CH2:27]1>>[CH2:10]([O:9][C:7]([N:4]1[CH2:5][CH2:6][C@H:2]([N:1]([CH2:23][CH3:24])[CH2:27][CH3:28])[CH2:3]1)=[O:8])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 4

HCID 6340IodoethaneHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 1519355(S)-1-Cbz-3-Aminopyrrolidine

Product 1

HCID 68693001(S)-1-(benzyloxycarbonyl)-3-(N,N-diethylamino)pyrrolidine

Procedure

To a solution of 1.40 g of (S)-3-amino-1-(benzyloxycarbonyl)pyrrolidine (J. Med. Chem., 1992, 35, 1764-1773) in 28 ml of tetrahydrofuran, 2.6 g of potassium carbonate and 1.0 ml of ethyl iodide were added under ice-cool stirring, followed by stirring for 24 hours. The reaction solution was concentrated under reduced pressure, mixed with water, followed by extraction with ethyl acetate, and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 0.70 g of the objective compound as a yellow oily product.

Workup

  1. temperaturecool
  2. stirringby stirring for 24 hours
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. additionmixed with water
  5. extractionfollowed by extraction with ethyl acetate
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2f4d393ee06c4c96bd870b37c357c585
Source dataset
uspto-grants-2010_06
Patent number
US07728131B2

Reaction notes

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