Methylamine → (1S,4S)-2-Methyl-5-tosyl-2,5-diazabicyclo[2.2.1]heptane

HRID 1087620Notes

Reaction equation

HRID 1087620 reaction equation
[C:1]1([CH3:38])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH2:14][C@H:13](OS(C3C=CC(C)=CC=3)(=O)=O)[CH2:12][C@H:11]2[CH2:26]OS(C2C=CC(C)=CC=2)(=O)=O)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:39][NH2:40]>CO>[C:1]1([CH3:38])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH2:14][C@@H:13]3[CH2:12][C@H:11]2[CH2:26][N:40]3[CH3:39])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 15629271(2S, 4R)-1-(4-toluenesulfonyl)-2-(p-toluenesulfonyl-oxymethyl)-4-(4-toluenesulfonyloxy)-pyrrolidine

Product 1

HCID 11054620(1S,4S)-2-Methyl-5-tosyl-2,5-diazabicyclo[2.2.1]heptaneYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
90 °C

Procedure

A Parr bottle was charged with 115 g (198.4 mmol) of (2S, 4R)-1-(4-toluenesulfonyl)-2-(p-toluenesulfonyl- oxymethyl)-4-(4-toluenesulfonyloxy)-pyrrolidine and 690 ml of methanol and the bottle was then tared. Methylamine gas was bubbled through the methanol solution until 62 g (2 mol) of the gas has dissolved. The bottle was then sealed and heated to 90° C. After heating for 16 hours the reaction was cooled and the solvent was evaporated at reduced pressure. The residual solids were then partitioned between 500 ml of methylene chloride and 400 ml of 10% aqueous sodium hydroxide solution. The layers were separated and the organic layer was washed with 400 additional ml of 10% aqueous sodium hydroxide solution, and then dried over sodium sulfate. Evaporation of the solvent under reduced pressure provided 47.5 g of the desired product which represents a 90% yield. M.P.=87°-88° C.

Workup

  1. dissolutionhas dissolved
  2. customThe bottle was then sealed
  3. temperatureAfter heating for 16 hours the reaction
  4. temperaturewas cooled
  5. customthe solvent was evaporated at reduced pressure
  6. customThe residual solids were then partitioned between 500 ml of methylene chloride and 400 ml of 10% aqueous sodium hydroxide solution
  7. customThe layers were separated
  8. washthe organic layer was washed with 400 additional ml of 10% aqueous sodium hydroxide solution
  9. dry with materialdried over sodium sulfate
  10. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-44e9730c8f6b418897bcafb42b883485
Source dataset
uspto-grants-1991_07
Patent number
US05036153

Reaction notes

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