Iodoethane → HCID 58312676, compound

HRID 527502Notes

Reaction equation

HRID 527502 reaction equation
[C:1]([O:5][C:6](=[O:27])[NH:7][C@H:8]1[C@H:12]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[CH2:11][N:10]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH2:31][CH3:32]>CN(C=O)C>[C:1]([O:5][C:6](=[O:27])[N:7]([C@H:8]1[C@H:12]([C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)[CH2:11][N:10]([CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:9]1)[CH2:31][CH3:32])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 45926020HCID 45926020, compound

Product 1

HCID 58312676HCID 58312676, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4.2 g (10.9 mmol) [(3S,4R)-1-Benzyl-4-(4-chloro-phenyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester, 521 mg (13 mmol) NaH (60%) and 2.54 g (16.3 mmol) iodoethane in 40 mL DMF was stirred for 1 h at 60° C. and evaporated to dryness. The residue was taken up in ethyl acetate and water and extracted further with ethyl acetate. The combined organic layers were washed with brine, dried with Na2SO4, filtered and evaporated to dryness. The residue was purified by column chromatography on silica eluting with a gradient formed from ethyl acetate and heptane to yield after evaporation of the product containing fractions 2.5 g (55%) of the title compound as light yellow viscous oil. MS m/e: 415.3 [M+H]+.

Workup

  1. customevaporated to dryness
  2. extractionwater and extracted further with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was purified by column chromatography on silica eluting with a gradient
  8. customformed from ethyl acetate and heptane
  9. customto yield
  10. customafter evaporation of the product
  11. additioncontaining fractions 2.5 g (55%) of the title compound as light yellow viscous oil

Sources & evidence

ORD record
ord-2e168f0ec1ef4b45950e665fd7655bfd
Source dataset
uspto-grants-2016_05
Patent number
US09346786B2

Reaction notes

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