Methylamine → HCID 57750283, compound

HRID 423083Notes

Reaction equation

HRID 423083 reaction equation
[CH3:1][NH2:2].CS(O[CH2:8][CH2:9][CH:10]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)(=O)=O>C1COCC1>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([CH:10]([NH:18][C:19](=[O:20])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:9][CH2:8][NH:2][CH3:1])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 57750403HCID 57750403, compound2×

Product 1

HCID 57750283HCID 57750283, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
125 °C

Procedure

Methylamine gas was bubbled into a solution of 3-(tert-butoxycarbonylamino)-3-(4-chlorophenyl)propyl methanesulfonate (Intermediate 31) (70 mg, 0.19 mmol) in THF (5 mL) at 22° C. over a period of 5 minutes. The mixture was sealed into a microwave tube. The reaction was heated to 125° C. for 30 minutes in the microwave reactor and cooled to ambient temperature. The mixture was evaporated and the residue was purified by flash silica chromatography, elution gradient 4 to 8% (10:1 MeOH/conc. NH3 (aq)) in DCM. Pure fractions were evaporated to dryness to afford tert-butyl 1-(4-chlorophenyl)-3-(methylamino)propylcarbamate (52 mg, 90%) as a colourless oil.

Workup

  1. customThe mixture was sealed into a microwave tube
  2. temperaturecooled to ambient temperature
  3. customThe mixture was evaporated
  4. customthe residue was purified by flash silica chromatography, elution gradient 4 to 8% (10:1 MeOH/conc. NH3 (aq)) in DCM
  5. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-f88f29b8ce70470897baef09ce33a268
Source dataset
uspto-grants-2012_01
Patent number
US08101623B2

Reaction notes

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