Iodocyclopentane → HCID 59527933, compound

HRID 2189971Notes

Reaction equation

HRID 2189971 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:19]1(I)[CH2:23][CH2:22][CH2:21][CH2:20]1>C1COCC1>[CH2:17]([O:16][C:14]([C:11]1([CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10]1)=[O:15])[CH3:18]

Participants

4

Reactant 2

HCID 73784IodocyclopentaneHCID 27588121-Tert-butyl 4-ethyl piperidine-1,4-dicarboxylate

Product 1

HCID 59527933HCID 59527933, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-75 °C

Procedure

A solution of 5 g ethyl 1-tert-butoxycarbonylpiperidine-4-carboxylate in 50 mL THF was added at −75° C. drop wise over 50 min. The yellow solution was stirred at −75° C. for 2 h. A solution of 4.5 g cyclopentyliodide in 20 mL THF was added drop wise over 45 min. The reaction was stirred at −75° C. for 1 h. The reaction was allowed to warm to room temperature over the weekend. The reaction was cooled to 0° C., quenched with 150 mL 10% citric acid solution. The aqueous layer was separated and extracted once with 150 mL ethyl acetate. The organic layers were washed with 100 mL brine, dried over Na2SO4, filtered and concentrated under vacuum. The crude product (yellow viscous oil, 7.75 g) was purified over silica chromatography eluting with a gradient formed from heptane and TBME to yield after evaporation of the product containing fractions 5.54 g (88%) of the title compound as colourless viscous oil. MS ISP (m/e): 326.3 [(M+H)+].

Workup

  1. stirringThe reaction was stirred at −75° C. for 1 h
  2. temperatureto warm to room temperature over the weekend
  3. temperatureThe reaction was cooled to 0° C.
  4. customquenched with 150 mL 10% citric acid solution
  5. customThe aqueous layer was separated
  6. extractionextracted once with 150 mL ethyl acetate
  7. washThe organic layers were washed with 100 mL brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under vacuum
  11. customThe crude product (yellow viscous oil, 7.75 g) was purified over silica chromatography
  12. washeluting with a gradient
  13. customformed from heptane and TBME
  14. customto yield
  15. customafter evaporation of the product
  16. additioncontaining fractions 5.54 g (88%) of the title compound as colourless viscous oil

Sources & evidence

ORD record
ord-63518f1c739645d09ff24bc19644e1f6
Source dataset
uspto-grants-2012_12
Patent number
US08324250B2

Reaction notes

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