Methylamine → HCID 14994790, compound

HRID 1614355Notes

Reaction equation

HRID 1614355 reaction equation
[C:1]([N:11]1[CH2:15][C@H:14](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:13][C@H:12]1[CH2:27]OS(C1C=CC(C)=CC=1)(=O)=O)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH3:39][NH2:40]>CO>[C:1]([N:11]1[CH2:15][C@@H:14]2[CH2:13][C@H:12]1[CH2:27][N:40]2[CH3:39])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 14994792(2S,4R)-benzyl 4-(tosyloxy)-2-((tosyloxy)methyl)pyrrolidine-1-carboxylate

Product 1

HCID 14994790HCID 14994790, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
80 °C

Procedure

A Parr bottle was charged with 22 g (40.2 mmol) of (2S,4R)-1-(carbobenzyloxy)-2-(p-toluenesulfonyloxymethyl)-4-(4-toluenesulfonyloxy)-pyrrolidine and 100 ml of methanol and the bottle was then tared. Methylamine gas was bubbled through the methanol solution until 12.4 g (402 mmol) of the gas had dissolved. The bottle was then sealed and heated to 80° 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 200 ml of methylene chloride and 150 ml of 10% aqueous NaOH solution. The layers were separated and the organic layer was washed with 100 additional ml of 10% aqueous NaOH solution, and then dried over Na2SO4. Evaporation of the solvent under reduced pressure provided 9.0 g of the desired product (oil) which represents a 91% yield. NMR(CDCl3): 7.32 (aromatic, 5H), 5.1 (d,2H), 4.4 (d,1H), 3.58 (dd, 1H), 3.4 (d,1H), 3.22 (m,1H), 2.88 (m,1H), 2.7 (d,1H), 2.52 (d,1H), 2.40 (s,3H), 1.86 (d,1H), 1.7 (m,1 H).

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 then partitioned between 200 ml of methylene chloride and 150 ml of 10% aqueous NaOH solution
  7. customThe layers were separated
  8. washthe organic layer was washed with 100 additional ml of 10% aqueous NaOH solution
  9. dry with materialdried over Na2SO4
  10. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-402b33ffeddc4f2282421f0cc80de909
Source dataset
uspto-grants-1993_03
Patent number
US05196548

Reaction notes

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