Benzyl 4-chloro-3-(diethoxyphosphorylamino)piperidine-1-carboxylate → Diethyl 4-chloropiperidin-3-ylphosphoramidate

HRID 73564Notes

Reaction equation

HRID 73564 reaction equation
[Cl:1][CH:2]1[CH2:7][CH2:6][N:5](C(OCC2C=CC=CC=2)=O)[CH2:4][CH:3]1[NH:18][P:19]([O:24][CH2:25][CH3:26])([O:21][CH2:22][CH3:23])=[O:20]>CO.[Pd]>[Cl:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH:3]1[NH:18][P:19](=[O:20])([O:24][CH2:25][CH3:26])[O:21][CH2:22][CH3:23]

Participants

4

Reactant 1

HCID 67500461Benzyl 4-chloro-3-(diethoxyphosphorylamino)piperidine-1-carboxylate

Product 1

HCID 67500859Diethyl 4-chloropiperidin-3-ylphosphoramidateYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

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+).

Workup

  1. filtrationThe solution was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-e38e766cd10e4fe78958f412fb6e4085
Source dataset
uspto-grants-2014_09
Patent number
US08829193B2

Reaction notes

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