N-methyl-N-((R)-1-(methylcarbamoyl)-2-phenylethyl)carbamic acid tert-butyl ester → (R)-N-methyl-2-(methylamino)-3-phenylpropanamide

HRID 366175Notes

Reaction equation

HRID 366175 reaction equation
C(O[C:6](=O)[N:7](C)[C@@H:8]([C:16](=[O:19])[NH:17][CH3:18])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(C)(C)C>FC(F)(F)C(O)=O.C(Cl)Cl>[CH3:18][NH:17][C:16](=[O:19])[C@H:8]([NH:7][CH3:6])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 1

HCID 10613603N-methyl-N-((R)-1-(methylcarbamoyl)-2-phenylethyl)carbamic acid tert-butyl ester

Product 1

HCID 10607786(R)-N-methyl-2-(methylamino)-3-phenylpropanamideYield 23.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

N-Methyl-N-((R)1-(methylcarbamoyl)-2-phenylethyl)carbamic acid tert-butyl ester (1.39 g, 7.23 mmol) was dissolved in a mixture of trifluoroacetic acid (5 mL) and methylene chloride (10 mL) and stirred for 45 min. The volatiles were removed in vacuo and the residue was stirred with a mixture of ethyl acetate (100 mL) and water (100 mL). Sodium hydrogen carbonate (50 mL, saturated) was added and the phases were separated. The organic phase was dried (magnesium sulfate) and the solvent removed in vacuo to afford 330 mg of (R)-N-methyl-2-methylamino-3-phenylpropionamide.

Workup

  1. customThe volatiles were removed in vacuo
  2. stirringthe residue was stirred with a mixture of ethyl acetate (100 mL) and water (100 mL)
  3. additionSodium hydrogen carbonate (50 mL, saturated) was added
  4. customthe phases were separated
  5. dry with materialThe organic phase was dried (magnesium sulfate)
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-170b500465104c5a85afac87832079e3
Source dataset
uspto-grants-2000_10
Patent number
US06127391

Reaction notes

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