Methylamine → HCID 15629278, compound

HRID 1087626Notes

Reaction equation

HRID 1087626 reaction equation
Cl[CH2:2][C@H:3]1[CH2:7][C@H:6](Cl)[CH2:5][N:4]1[S:9]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10].[CH3:19][NH2:20]>CO>[C:15]1([CH3:18])[CH:16]=[CH:17][C:12]([S:9]([N:4]2[CH2:5][C@H:6]3[CH2:7][C@@H:3]2[CH2:2][N:20]3[CH3:19])(=[O:11])=[O:10])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 14994789(2R,4S)-2-chloromethyl-4-chloro-1-(4-toluenesulfonyl)pyrrolidine

Product 1

HCID 15629278HCID 15629278, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
110 °C

Procedure

A Parr bottle was charged with 0.5 g (1.29 :mmol) of (2R,4S)-2-chloromethyl-4-chloro-1-(4-toluenesulfonyl)pyrrolidine and 6 ml of methanol and the bottle was tared. Methylamine gas was then bubbled through the methanol solution until 0.4 g (12.9 mol) of the gas had dissolved. The bottle was then sealed and heated to 110° C. After heating for 16 hours, the reaction was cooled and the solvent was evaporated at reduced pressure. The residual solids were partitioned between 50 ml of methylene chloride and 40 ml of 10% aqueous NaOH solution. The layers were separated and the organic layer was washed with 40 additional milliliters of 10% aqueous NaOH solution, and then dried over Na2SO4. Evaporation of the solvent under reduced pressure provided 309 mg of the desired product which represents a 90% yield. M.P.=82°-87° C. [α]D =-16.8° (c=1.038, CH3OH).

Workup

  1. dissolutionhad dissolved
  2. customThe bottle was then sealed
  3. temperatureAfter heating for 16 hours
  4. temperaturethe reaction was cooled
  5. customthe solvent was evaporated at reduced pressure
  6. customThe residual solids were partitioned between 50 ml of methylene chloride and 40 ml of 10% aqueous NaOH solution
  7. customThe layers were separated
  8. washthe organic layer was washed with 40 additional milliliters of 10% aqueous NaOH solution
  9. dry with materialdried over Na2SO4
  10. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-23b0639d588b4ebca758231262940213
Source dataset
uspto-grants-1991_07
Patent number
US05036153

Reaction notes

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