HCID 86615897, compound → [4-(2-Amino-1-aminomethyl-ethyl)-phenyl]-carbamic acid tert-butyl ester

HRID 340541Notes

Reaction equation

HRID 340541 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH2:19][N:20]=[N+]=[N-])[CH2:15][N:16]=[N+]=[N-])=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]>[Pd]>[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH2:15][NH2:16])[CH2:19][NH2:20])=[CH:10][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 86615897HCID 86615897, compound

Product 1

HCID 59771216[4-(2-Amino-1-aminomethyl-ethyl)-phenyl]-carbamic acid tert-butyl esterYield 84.1%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

[4-(2-Azido-1-azidomethyl-ethyl)-phenyl]-carbamic acid tert-butyl ester (240 mg, 0.757 mmol, as prepared above) was hydrogenated at 40 psi H2 over 10% Pd/C (120 mg) for 1 h. The reaction mixture was filtered through a pad of Celite, concentrated and dried in vacuo to afford [4-(2-amino-1-aminomethyl-ethyl)-phenyl]-carbamic acid tert-butyl ester (169 mg, 64%): 1H-NMR (CD3OD; 400 MHz): δ 7.35 (d, 2H, J=8.6 Hz), 7.12 (d, 2H, J=8.6 Hz), 2.90 (m, 2H), 2.79 (m, 2H), 2.69 (m, 1H), 1.42 (s, 9H).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. concentrationconcentrated
  3. customdried in vacuo

Sources & evidence

ORD record
ord-d859c980a1684b969f64378bab4e6da2
Source dataset
uspto-grants-2014_11
Patent number
US08895584B2

Reaction notes

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