Reaction #160746

ord-e38e766cd10e4fe78958f412fb6e4085

Reaction equation

CCOP(=O)(NC1CN(C(=O)OCc2ccccc2)CCC1Cl)OCC
benzyl 4-chloro-3-(diethoxyphosphorylamino)piperidine-1-carboxylate
→
CCOP(=O)(NC1CNCCC1Cl)OCC
diethyl 4-chloropiperidin-3-ylphosphoramidate
Yield 92.0%

Reactants

CCOP(=O)(NC1CN(C(=O)OCc2ccccc2)CCC1Cl)OCC
benzyl 4-chloro-3-(diethoxyphosphorylamino)piperidine-1-carboxylate

Reagents

[Pd]
Pd/C

Solvents

CO
MeOH

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    FiltrationThe solution was filtered
  2. 2
    Concentrationconcentrated

Procedure

To a solution of benzyl 4-chloro-3-(diethoxyphosphorylamino)piperidine-1-carboxylate (1.0 equiv.) in degassed MeOH was added Pd/C (10% by weight) and the reaction was stirred under a hydrogen atmosphere for 1 h. The solution was filtered, then concentrated to yield diethyl 4-chloropiperidin-3-ylphosphoramidate in 92% yield. LCMS (m/z): 271.0 (MH+).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08829193B2uspto-grants-2014_09