benzyl N-[(2S)-2-hydroxy-3-(4-methylpiperazin-1-yl)propyl]carbamate → (2S)-1-amino-3-(4-methylpiperazin-1-yl)propan-2-ol

HRID 2364713Notes

Reaction equation

HRID 2364713 reaction equation
[OH:1][C@H:2]([CH2:15][N:16]1[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]1)[CH2:3][NH:4]C(=O)OCC1C=CC=CC=1>CO.[Pd]>[NH2:4][CH2:3][C@H:2]([OH:1])[CH2:15][N:16]1[CH2:17][CH2:18][N:19]([CH3:22])[CH2:20][CH2:21]1

Participants

4

Reactant 1

HCID 68106686benzyl N-[(2S)-2-hydroxy-3-(4-methylpiperazin-1-yl)propyl]carbamate

Product 1

HCID 28279112(2S)-1-amino-3-(4-methylpiperazin-1-yl)propan-2-olYield 106.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Benzyl N-[(2S)-2-hydroxy-3-(4-methylpiperazin-1-yl)propyl]carbamate 21b (840 mg, 2.70 mmol) was dissolved in 50 mL of methanol to prepare a 0.01 mol/L solution. The reaction solution was hydrogenated with H-Cube (column of catalyst: 10% palladium/carbon; temperature: 30° C.; flow rate: 1 mL/min; pressure: 1 atmosphere) for 50 minutes. The reaction solution was concentrated under reduced pressure to obtain the crude title compound (2S)-1-amino-3-(4-methylpiperazin-1-yl)propan-2-ol 21c (500 mg) as a yellow oil which was used in the next step without further purification.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c9e21b50b34742f1a25b76618152cd5d
Source dataset
uspto-grants-2014_04
Patent number
US08691822B2

Reaction notes

Loading…