Reaction #487549

ord-37894b280e3346f6b37966794973c92d

Reaction equation

CN1CCc2cc(N3C[C@@H](CN=[N+]=[N-])OC3=O)ccc2C1
(S)-5-azidomethyl-3-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-6-yl)-oxazolidin-2-one
[H][H]
hydrogen
CN1CCc2cc(N3C[C@H](CN)OC3=O)ccc2C1
(S)-5-aminomethyl-3-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-6-yl)-oxazolidin-2-one

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    FiltrationThe catalyst is filtered off
  2. 2
    Otherthe filtrate is evaporated to dryness i

Procedure

184 mg (0.6 mmol) (S)-5-azidomethyl-3-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-6-yl)-oxazolidin-2-one are dissolved in a mixture of 2 ml THF and 10 ml of methanol, combined with 50 mg palladium/charcoal (5%) and hydrogenated for two hours at 3 bar hydrogen pressure. The catalyst is filtered off and the filtrate is evaporated to dryness i. vac.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08741890B2uspto-grants-2014_06