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

HRID 2364709Notes

Reaction equation

HRID 2364709 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.[H][H]>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

5

Reactant 2

HCID 68108054benzyl N-[(2R)-2-hydroxy-3-(4-methylpiperazin-1-yl)propyl]carbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 28279114(2R)-1-amino-3-(4-methylpiperazin-1-yl)propan-2-olYield 106.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Benzyl N-[(2R)-2-hydroxy-3-(4-methylpiperazin-1-yl)propyl]carbamate 20d (830 mg, 2.70 mmol) was dissolved in 40 mL of methanol followed by the addition of palladium/carbon (85 mg, 10%), filled with hydrogen three times. The reaction solution was stirred for 12 hours and filtered. The filtrate was concentrated under reduced pressure to obtain the crude title compound (2R)-1-amino-3-(4-methylpiperazin-1-yl)propan-2-ol 20e (500 mg) as a light yellow oil, which was used in the next step without further furification.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-cca94c7489ee499f94888eb3960ca14b
Source dataset
uspto-grants-2014_04
Patent number
US08691822B2

Reaction notes

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