Iodoethane → HCID 70983521, compound

HRID 928004Notes

Reaction equation

HRID 928004 reaction equation
[CH3:1][N:2]([C@H:13]1[CH2:17][CH2:16][NH:15][CH2:14]1)[C:3](=[O:12])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.I[CH2:19][CH3:20].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:19]([N:15]1[CH2:16][CH2:17][C@H:13]([N:2]([CH3:1])[C:3](=[O:12])[O:4][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:14]1)[CH3:20]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 66569359HCID 66569359, compound2×

Product 1

HCID 70983521HCID 70983521, compoundYield 47.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of benzyl N-methyl-(S)-pyrrolidin-3-ylcarbamate (Intermediate 129, 1.28 g), iodoethane (0.853 g), and potassium carbonate (1.51 g) in acetonitrile (12 mL) was stirred at room temperature for 4 hours. The mixture was evaporated in vacuo and the residue was basified with 5M sodium hydroxide and filtered through a phase separator. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of methanol and DCM with a gradient of 0-30% to give benzyl N—((S)-1-ethylpyrrolidin-3-yl)-N-methylcarbamate (0.686 g) as a colourless oil.

Workup

  1. customThe mixture was evaporated in vacuo
  2. filtrationfiltered through a phase separator
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by chromatography on silica
  5. washeluting with a mixture of methanol and DCM with a gradient of 0-30%

Sources & evidence

ORD record
ord-900d90d405f34c0fadab535110148727
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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