Hydrochloric Acid → HCID 15672690, compound

HRID 1656650Notes

Reaction equation

HRID 1656650 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[C:3](Cl)=[O:4].[F:8][C:9]([F:17])([F:16])[C:10]1([CH3:15])[CH2:14][CH2:13][CH2:12][NH:11]1.C(N(CC)CC)C.Cl>C1COCC1>[C:3]([N:11]1[CH2:12][CH2:13][CH2:14][C:10]1([C:9]([F:17])([F:16])[F:8])[CH3:15])(=[O:4])[C:2]([CH3:7])([CH3:6])[CH3:1]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 15672688141519-24-6

Product 1

HCID 15672690HCID 15672690, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 6.03 g (0.05 mol) of 2,2-dimethylpropionyl chloride in 25 ml of THF was added dropwise to a solution of 7.65 g (0.05 mol) of 2-trifluoromethyl-2-methylpyrrolidine in 15 ml of THF, to which 5.6 g (0.055 mol) of triethylamine had been added. The course of the reaction is exothermic. The dropwise addition was effected slowly enough that the temperature did not rise to above 35° C. Stirring was continued for one hour at room temperature, and the mixture was then poured into 200 ml of ice-water, the pH was adjusted to 4-5 using dilute hydrochloric acid, and the mixture was extracted twice using 60 ml portions of dichloromethane. The combined organic phases were dried over magnesium sulphate and filtered, and the solvent was stripped off under a water pump vacuum. The oil which remained was chromatographed over a short silica gel column (mobile phase toluene/ethyl acetate 1:1). After the mobile phase had been removed, 9.12 g (77% yield of theory) of N-pivaloyl-2-trifluoromethyl-2-methylpyrrolidine are obtained as a pale yellow oil having a refractive index of nD20 : 1,4615 (GC purity: 97.7%).

Workup

  1. additionhad been added
  2. additionThe dropwise addition
  3. customdid not rise to above 35° C
  4. extractionthe mixture was extracted twice
  5. dry with materialThe combined organic phases were dried over magnesium sulphate
  6. filtrationfiltered
  7. customThe oil which remained was chromatographed over a short silica gel column (mobile phase toluene/ethyl acetate 1:1)
  8. customAfter the mobile phase had been removed

Sources & evidence

ORD record
ord-9bf3a2b98e8f41658f667e1b52d4e06a
Source dataset
uspto-grants-1993_10
Patent number
US05254696

Reaction notes

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