Ethanol → tert-butyl N-[2-amino-1-(4-chlorophenyl)ethyl]carbamate

HRID 423087Notes

Reaction equation

HRID 423087 reaction equation
CS(O[CH2:6][CH:7]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)(=O)=O.[N-:23]=[N+]=[N-].[Na+].C(O)C>CN(C=O)C.[Pd]>[NH2:23][CH2:6][CH:7]([NH:15][C:16](=[O:17])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 33557Sodium AzideHCID 577502782-(Tert-butoxycarbonylamino)-2-(4-chlorophenyl)ethyl methanesulfonate2×

Product 1

HCID 57750386tert-butyl N-[2-amino-1-(4-chlorophenyl)ethyl]carbamateYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 2-(tert-butoxycarbonylamino)-2-(4-chlorophenyl)ethyl methanesulfonate (Intermediate 23) (535 mg, 1.53 mmol) in DMF (8 mL) was treated with sodium azide (199 mg, 3.06 mmol) and the mixture was heated at 80° C. for 1 hour. The mixture was cooled and allowed to stir at room temperature overnight. The solution was partitioned between ethyl acetate and water. The organic layer was washed twice with water then dried with magnesium sulfate, filtered and concentrated until the final volume was approximately 5 mL. Ethanol (20 mL) and 10% palladium on carbon (75 mg, 0.07 mmol) were added. The resulting suspension was stirred under an atmosphere of hydrogen at ambient pressure and temperature for 1 hour. The mixture was filtered and the filtrate was concentrated under reduced pressure to give tert-butyl 2-amino-1-(4-chlorophenyl)ethylcarbamate as a gum (410 mg, 99%).

Workup

  1. temperatureThe mixture was cooled
  2. customThe solution was partitioned between ethyl acetate and water
  3. washThe organic layer was washed twice with water
  4. dry with materialthen dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated until the final volume
  7. stirringThe resulting suspension was stirred under an atmosphere of hydrogen at ambient pressure and temperature for 1 hour
  8. filtrationThe mixture was filtered
  9. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-32c5a0e8da454e40985b831be5d49397
Source dataset
uspto-grants-2012_01
Patent number
US08101623B2

Reaction notes

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