4-Toluenesulfonyl chloride → HCID 86612725, compound

HRID 1671711Notes

Reaction equation

HRID 1671711 reaction equation
[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:8]2[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1>C(Cl)Cl>[C:14]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[CH2:12][CH2:11][C@H:10]([O:13][S:33]([C:30]3[CH:31]=[CH:32][C:27]([CH3:37])=[CH:28][CH:29]=3)(=[O:35])=[O:34])[CH2:9]2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chloride2×HCID 8471Triethylamine2×HCID 25242003HCID 25242003, compound

Product 1

HCID 86612725HCID 86612725, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3S)-1-Diphenylmethyl-3-hydroxypyrrolidine (4.00 g) was dissolved in methylene chloride (11 mL), and the solution was stirred under cooling with ice. Triethylamine (3.3 mL) was added dropwise to the reaction mixture, and p-toluenesulfonyl chloride (3.61 g) was added to the resultant mixture, followed by stirring at room temperature for 12 hours and then at 40° C. for 4.5 hours. Since the starting materials partially remained unconsumed, triethylamine (1.1 mL) and p-toluenesulfonyl chloride (1.5 g) were added to the reaction mixture and then stirred for 24 hours. The reaction mixture was extracted with water and chloroform, and the organic layer was dried over sodium sulfate. The drying agent was removed through filtration, and the filtrate was concentrated under reduced pressure, to thereby yield crystalline residue. The residue was subjected to silica gel chromatography, to thereby give the target compound (4.40 g, yield 68.5%). The thus-obtained compound was purified through recrystallization from isopropyl alcohol.

Workup

  1. temperatureunder cooling with ice
  2. stirringby stirring at room temperature for 12 hours
  3. stirringstirred for 24 hours
  4. extractionThe reaction mixture was extracted with water and chloroform
  5. dry with materialthe organic layer was dried over sodium sulfate
  6. customThe drying agent was removed through filtration
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c8d6cafea8444c53be479391c7bc3943
Source dataset
uspto-grants-2011_08
Patent number
US07994344B2

Reaction notes

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