Iodoethane → HCID 53256801, compound

HRID 927967Notes

Reaction equation

HRID 927967 reaction equation
[NH:1]1[CH2:5][CH2:4][C@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:2]1.I[CH2:15][CH3:16].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:15]([N:1]1[CH2:5][CH2:4][C@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:12])[CH3:11])[CH2:2]1)[CH3:16]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 1514396(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidine

Product 1

HCID 53256801HCID 53256801, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of tert butyl (S)-pyrrolidin-3-ylcarbamate (1.048 g), iodoethane (0.90 g) and potassium carbonate (1.55 g) in acetonitrile (15 mL) was stirred at room temperature for 17 hours then filtered. The filtrate was concentrated in vacuo and the residue was triturated with DCM and filtered. 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 0-35% to give tert-butyl ((S)-1-ethylpyrrolidin-3-yl)carbamate (0.891 g) as a light coloured gum.

Workup

  1. filtrationthen filtered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue was triturated with DCM
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was purified by chromatography on silica
  7. washeluting with a mixture of methanol and DCM with a gradient of 0-35%

Sources & evidence

ORD record
ord-3a721e1b9cd2477d89f79a5f5349e837
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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