Toluene → HCID 117849117, compound

HRID 1477632Notes

Reaction equation

HRID 1477632 reaction equation
C1(C)C=CC=CC=1.[F:8][C:9]1[CH:14]=[CH:13][C:12]([C@:15]2(O)[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][C@H:16]2[O:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:11][CH:10]=1.C([N+](CC)(CC)S(NC(=O)OC)(=O)=O)C>C(OCC)(=O)C>[F:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[C@H:16]([O:28][C:29](=[O:34])[C:30]([CH3:31])([CH3:32])[CH3:33])[CH2:17][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:19][CH:20]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 2724995Triethyl(methoxycarbonylsulfamoyl)aminiumHCID 117849081HCID 117849081, compound

Product 1

HCID 117849117HCID 117849117, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a toluene solution (40 mL) of tert-butyl (3R,4R)-4-(4-fluorophenyl)-4-hydroxy-3-(pivaloyloxy)piperidine-1-carboxylate (2.04 g, 5.16 mmol) synthesized in Reference Synthesis Example 135, methyl N-(triethylammoniosulfonyl)carbamate (1.72 g, 7.22 mmol) was added and the resultant mixture was stirred at 60° C. for 3 hours. After completion of the reaction, ethyl acetate was added to the reaction solution and the resultant mixture was washed with each of saturated sodium bicarbonate aqueous solution and saturated sodium chloride aqueous solution. The obtained organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1→3/1) to obtain the title compound (1.82 g, yield 93%).

Workup

  1. additionwas added
  2. additionwas added to the reaction solution
  3. washthe resultant mixture was washed with each of saturated sodium bicarbonate aqueous solution and saturated sodium chloride aqueous solution
  4. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1→3/1)

Sources & evidence

ORD record
ord-fa1f21f468694a0bbf0097e269dab12b
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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