HCID 23000556, compound → HCID 23000589, compound

HRID 397480Notes

Reaction equation

HRID 397480 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:28]=[CH:27][CH:26]=[CH:25][C:12]=1[CH2:13][NH:14]C(=O)OCC1C=CC=CC=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[NH2:14][CH2:13][C:12]1[CH:25]=[CH:26][CH:27]=[CH:28][C:11]=1[CH2:10][CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 1

HCID 23000556HCID 23000556, compound

Product 1

HCID 23000589HCID 23000589, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 750 mg (1.95 mmol) benzyl 2-{2-[(tert-butoxycarbonyl) amino]ethyl}benzylcarbamate in 6.0 mL absolute ethanol was added 150 mg of 10% palladium on carbon catalyst. A balloon of hydrogen was bubbled into the stirring suspension at room temperature over 2 h. The reaction was filtered through celite and the filter pad washed with fresh absolute ethanol (2×). The filtrate was concentrated to dryness in vacuo to give tert-butyl 2-[2-(aminomethyl)phenyl]ethylcarbamate as a colorless oil: 1H NMR (CDCl3, 400 MHz): δ7.31-7.19 (m, 4H), 5.68 (br s, 1H), 3.90 (s, 2H), 3.41-3.34 (br m, 2H), 2.90-2.83 (br t, 2H, J=6.8 Hz), 1.41 (s, 9H); MS (Electrospray): M+NH=251.1; TLC Rf=0.24 (160/10/1 of methylene chloride/methanol/concentrated ammonium hydroxide).

Workup

  1. customA balloon of hydrogen was bubbled into the stirring suspension at room temperature over 2 h
  2. filtrationThe reaction was filtered through celite
  3. washthe filter pad washed with fresh absolute ethanol (2×)
  4. concentrationThe filtrate was concentrated to dryness in vacuo

Sources & evidence

ORD record
ord-0e1e77fb43d04b859fdff773960923d4
Source dataset
uspto-grants-2003_08
Patent number
US06610701B2

Reaction notes

Loading…