p-Toluenesulfonic acid → HCID 13504836, compound

HRID 1906427Notes

Reaction equation

HRID 1906427 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:17]=[CH:16][C:6]([C:7]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]2=O)=[O:8])=[CH:5][CH:4]=1.[NH:20]1[CH2:23][CH2:22][CH2:21]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[F:1][C:2]([F:19])([F:18])[C:3]1[CH:17]=[CH:16][C:6]([CH:7]([OH:8])[CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]2[N:20]2[CH2:23][CH2:22][CH2:21]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 10422AzetidineHCID 202118992-[4-(Trifluoromethyl)benzoyl]cyclohexan-1-one

Product 1

HCID 13504836HCID 13504836, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2-[4-(trifluoromethyl)benzoyl]cyclohexanone, 5.4 g, 0.02 mole, with 2.28 g, 0.04 mole of azetidine and 25 mg of p-toluenesulfonic acid in 50 ml of benzene was refluxed for 17 hr using a Soxhlet device containing 50 g of 3 A molecular sieves. The resulting solution was evaporated, the residue was dissolved in 75 ml of ethanol and hydrogenated in the presence of 0.5 g of platinum dioxide (PtO2) at an initial pressure of 54 psig for 1.5 hr. The mixture was filtered, cooled in ice and treated with 5.4 g of sodium borohydride (NaBH4) and stirred at room temperature for 16 hr. The mixture was then evaporated, the residue taken up in a water/diethyl ether mixture, the ether extract being separated and washed with saturated sodium chloride solution, dried with magnesium sulfate and evaporated. Trituration of the residue with diethyl ether gave 0.76 g (plus filtrate) of the N-[2-[[4 -(trifluoromethyl)phenyl](hydroxy)methyl]cyclohexyl]azetidine as a colorless solid, mp 163°-165° C., which was raised to 167°-168° C. on recrystallization from methanol. The UV λmax(ε)216-(9,550), 252(382), 258(442), 263(411), 258(307). The IR and Mass spectral analyses were consistent. The NMR (CDCl3) indicated that the product contained a mixture of two diastereoisomers. δ7.6-7.4 (m, 5H, aromatic) 5.1 (m, 1H, HC--O) 2.7 (m, 1H, CH--N) 2.2-1.9 (m, 3H, CH'C--O and C--CH2 --C of azetidine) 1.9-0.9 (m, 8H, CH2 's).

Workup

  1. customThe resulting solution was evaporated
  2. dissolutionthe residue was dissolved in 75 ml of ethanol and hydrogenated in the presence of 0.5 g of platinum dioxide (PtO2) at an initial pressure of 54 psig for 1.5 hr
  3. filtrationThe mixture was filtered
  4. temperaturecooled in ice
  5. additiontreated with 5.4 g of sodium borohydride (NaBH4)
  6. customThe mixture was then evaporated
  7. extractionthe ether extract
  8. custombeing separated
  9. washwashed with saturated sodium chloride solution
  10. dry with materialdried with magnesium sulfate
  11. customevaporated

Sources & evidence

ORD record
ord-99b06a45c368478cb144fbd11f7307d3
Source dataset
uspto-grants-1987_03
Patent number
US04652559

Reaction notes

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