Tert-butyl N-[2-(4-nitrophenyl)ethyl]carbamate → Tert-butyl 4-aminophenethylcarbamate

HRID 990074Notes

Reaction equation

HRID 990074 reaction equation
[N+:1]([C:4]1[CH:19]=[CH:18][C:7]([CH2:8][CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:6][CH:5]=1)([O-])=O.[H][H].CCCCCC.C(OCC)(=O)C>C(O)C.C1COCC1.[Pd]>[NH2:1][C:4]1[CH:19]=[CH:18][C:7]([CH2:8][CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:14])[CH3:15])=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 10264884Tert-butyl N-[2-(4-nitrophenyl)ethyl]carbamateHCID 21226206Ethyl acetate hexaneHCID 178418361HCID 178418361, compound

Product 1

HCID 382207Tert-butyl 4-aminophenethylcarbamateYield 84.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(tert-butoxycarbonyl)-4-nitrophenethyl-2-amine from Example 2 (24.2 g, 96.7 mmol) in a mixture of ethanol (150 mL) and THF (50 mL) was added 5% Pd/C (4.0 g). This solution was placed on a Parr Hydrogenator under 40 psig of hydrogen gas and shaken for 5 hours. The reaction mixture was filtered and evaporated to leave a colorless oil. This oil was taken up into hot hexane/ethyl acetate and allowed to crystallized overnight. The solid was collected via vacuum filtration and placed under high vacuum for eight hours. 19.31 g of the title compound, as a white solid, was obtained.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated
  3. customto leave a colorless oil
  4. customto crystallized overnight
  5. filtrationThe solid was collected via vacuum filtration
  6. waitplaced under high vacuum for eight hours

Sources & evidence

ORD record
ord-a697d1e9887245f3ba25d9b0a84a8fec
Source dataset
uspto-grants-2002_10
Patent number
US06458817B1

Reaction notes

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