Benzyl 4-(2-(di-tert-butoxyphosphoryloxy)ethyl)piperazine-1-carboxylate → Di-tert-butyl 2-(piperazin-1-yl)ethyl phosphate

HRID 1771192Notes

Reaction equation

HRID 1771192 reaction equation
[C:1]([O:5][P:6]([O:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][N:19](C(OCC2C=CC=CC=2)=O)[CH2:18][CH2:17]1)([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[P:6]([O:13][CH2:14][CH2:15][N:16]1[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]1)([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])([O:8][C:9]([CH3:10])([CH3:11])[CH3:12])=[O:7]

Participants

4

Reactant 1

HCID 58080081Benzyl 4-(2-(di-tert-butoxyphosphoryloxy)ethyl)piperazine-1-carboxylate2×

Product 1

HCID 58080136Di-tert-butyl 2-(piperazin-1-yl)ethyl phosphateYield 99.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A 100 ml flask was charged with benzyl 4-(2-(di-tert-butoxyphosphoryloxy)ethyl)piperazine-1-carboxylate (INTERMEDIATE 58, 0.90 g, 1.97 mmol) in MeOH (19.7 ml) and 10% palladium on charcoal (0.042 g, 0.04 mmol). The reaction mixture was stirred under a hydrogen atmosphere overnight. The reaction mixture was filtered and the filtrate concentrated in vacuo to give the title compound (0.63 g, yield: 99%), which was used in the preparation of INTERMEDIATE 61 without further purification.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-8a710a75070e45b6b19ff853047b8834
Source dataset
uspto-grants-2016_02
Patent number
US09248140B2

Reaction notes

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