Dichloromethane → (R)-2-(4-methoxybenzoylamino)-2-phenylethylamine

HRID 23954Notes

Reaction equation

HRID 23954 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([C:7]([NH:9][C@H:10]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:11][N:12]=[N+]=[N-])=[O:8])=[CH:5][CH:4]=1.C(Cl)Cl.C(OCC)(=O)C>[Pd].C1COCC1.CO>[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([C:7]([NH:9][C@H:10]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:11][NH2:12])=[O:8])=[CH:5][CH:4]=1

Participants

7

Reactant 3

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 53998160(R)-2-(4-Methoxybenzoylamino)-2-phenylethylazide

Product 1

HCID 54421380(R)-2-(4-methoxybenzoylamino)-2-phenylethylamineYield 84%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

(R)-2-(4-methoxybenzoylamino)-2-phenylethyl azide (46.3 g) was combined with 10% palladium on carbon in THF (400 mL), methanol (100 mL) and was stirred under a hydrogen atmosphere. Analysis by TLC (70% methylene chloride, ethyl acetate) indicated absence of starting material after stirring overnight. The solution was filtered through diatomaceous earth, rinsed with THF, and evaporated. The resulting solid was recrystallized with ethyl acetate, and dried under vacuum at 60° C. for 1 h to afford 35.4 g (84%) of a white crystalline solid.

Workup

  1. stirringafter stirring overnight
  2. filtrationThe solution was filtered through diatomaceous earth
  3. washrinsed with THF
  4. customevaporated
  5. customThe resulting solid was recrystallized with ethyl acetate
  6. customdried under vacuum at 60° C. for 1 h

Sources & evidence

ORD record
ord-f617e1f8d1bf48c58b8ab056d9ae01f2
Source dataset
uspto-grants-2005_02
Patent number
US06855715B1

Reaction notes

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