1,1,1-Trifluoro-2-iodoethane → HCID 59527747, compound

HRID 2189985

Reaction equation

HRID 2189985 reaction equation
C([CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][N:4]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])C.[F:16][C:17]([F:21])([F:20])[CH2:18]I>C1COCC1>[CH2:12]([O:11][C:9]([C:7]1([CH2:18][C:17]([F:21])([F:20])[F:16])[CH2:8][CH2:3][N:4]([C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[CH2:5][CH2:6]1)=[O:10])[CH3:13]

Participants

4

Reactant 2

HCID 677091,1,1-Trifluoro-2-iodoethaneHCID 12170201tert-Butyl 2-Ethylpiperidine-1-carboxylate

Product 1

HCID 59527747HCID 59527747, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

Under a argon atmosphere a vacuum dried 750 mL four necked flask (with mechanical stirrer) was charged with 6.6 mL diisopropylamine and 100 mL THF. The solution was cooled to −5° C./−10° C. 29.1 mL of 1.6M n-butyllithium in hexane was added over a period of 20 min. The light yellow solution was stirred for 30 min at −5°/−10° C. and afterwards cooled to −75° C. A solution of 10 g (38.8 mmol) ethyl 1-tert-butoxycarbonylpiperidine in 75 mL THF was added over a period of 50 min. The yellow solution was stirred at −75° C. for 2 h. A solution of 9.8 g (46.7 mmol) 2,2,2-trifluoroethyl iodide in 25 mL THF was added dropwise over a period of 45 min. The reaction was stirred for 1 h at −75° C. and allowed to warm up over night to ambient temperature. The reaction was cooled down to 0° C., quenched with 250 mL 10% citric acid aq. solution The aqueous layer was separated and extracted twice with 200 mL ethyl acetate. The organic layers were washed once with 200 mL brine, dried over Na2SO4, filtered and evaporated.

Workup

  1. dry with materialUnder a argon atmosphere a vacuum dried 750 mL four necked flask (with mechanical stirrer)
  2. additionwas charged with 6.6 mL diisopropylamine and 100 mL THF
  3. addition29.1 mL of 1.6M n-butyllithium in hexane was added over a period of 20 min
  4. temperatureafterwards cooled to −75° C
  5. stirringThe yellow solution was stirred at −75° C. for 2 h
  6. stirringThe reaction was stirred for 1 h at −75° C.
  7. temperatureto warm up over night to ambient temperature
  8. temperatureThe reaction was cooled down to 0° C.
  9. customquenched with 250 mL 10% citric acid aq. solution The aqueous layer
  10. customwas separated
  11. extractionextracted twice with 200 mL ethyl acetate
  12. washThe organic layers were washed once with 200 mL brine
  13. dry with materialdried over Na2SO4
  14. filtrationfiltered
  15. customevaporated

Sources & evidence

ORD record
ord-f47a936172344928aaa9b62cce57a353
Source dataset
uspto-grants-2012_12
Patent number
US08324250B2

Linked notes

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