Methanol → HCID 59364376, compound

HRID 426056Notes

Reaction equation

HRID 426056 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]([CH2:21][CH2:22][C:23]#[N:24])[C:9](=O)[CH2:10][N:11]([CH3:19])[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:5]=[CH:6][CH:7]=1.CO>C1COCC1>[NH2:24][CH2:23][CH2:22][CH2:21][N:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[CH2:9][CH2:10][N:11]([CH3:19])[C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 887MethanolHCID 66704443HCID 66704443, compound

Product 1

HCID 59364376HCID 59364376, compoundYield 104,465.602%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

tert-butyl 2-((3-chlorophenyl)(2-cyanoethyl)amino)-2-oxoethyl(methyl)carbamate (500 mg, 1.4 mmol) was dissolved in anhydrous THF (10 mL) and heated to reflux under nitrogen atmosphere. A solution of BH3.MeS in THF was added drop wise and stirring was continued under reflux overnight. The resulting solution was cooled to room temperature. Methanol was added drop wise to quench the reaction. After evaporation of the solution, the crude product was purified by column chromatography to afford the pure product tert-butyl 2-((3-aminopropyl)(3-chlorophenyl)amino)ethyl(methyl)carbamate (500 g, yield 99%).

Workup

  1. temperatureheated
  2. temperatureto reflux under nitrogen atmosphere
  3. temperatureunder reflux overnight
  4. customto quench
  5. customthe reaction
  6. customAfter evaporation of the solution
  7. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-874be62937cf4614be1f9aab0eb2308f
Source dataset
uspto-grants-2012_01
Patent number
US08106221B2

Reaction notes

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