HCID 101175893, compound → HCID 67045454, compound

HRID 875640Notes

Reaction equation

HRID 875640 reaction equation
[CH:1]1([C@@H:4]2[CH2:9][CH2:8][N:7](C(OCC3C=CC=CC=3)=O)[CH2:6][C@H:5]2[NH:20][P:21]([O:26][CH2:27][CH3:28])([O:23][CH2:24][CH3:25])=[O:22])[CH2:3][CH2:2]1.[H][H]>CO.[Pd]>[CH:1]1([C@@H:4]2[CH2:9][CH2:8][NH:7][CH2:6][C@H:5]2[NH:20][P:21](=[O:22])([O:23][CH2:24][CH3:25])[O:26][CH2:27][CH3:28])[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 101175893HCID 101175893, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67045454HCID 67045454, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of trans-benzyl 4-cyclopropyl-3-(diethoxyphosphorylamino)piperidine-1-carboxylate (1.84 g, 4.48 mmol) and 10% Pd/C (0.48 g, 0.45 mmol) in methanol (30 mL) was charged with 1 atmosphere hydrogen and stirred at room temperature for 1 hour. The catalyst was removed by filtration and washed with methanol (20 mL). The filtrate was concentrated in vacuo to give diethyl trans-4-cyclopropylpiperidin-3-ylphosphoramidate (1.24 g, 100%) as an oil.

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with methanol (20 mL)
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-ec9e1680f38e4106a8174d2b5781a1a3
Source dataset
uspto-grants-2015_03
Patent number
US08981085B2

Reaction notes

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