2-Methyl-3-(methylamino)-2-nitropropan-1-ol hydrochloride → 2-Amino-2-methyl-3-(methylamino)propan-1-ol hydrochloride

HRID 1025922Notes

Reaction equation

HRID 1025922 reaction equation
[ClH:1].[CH3:2][C:3]([N+:9]([O-])=O)([CH2:6][NH:7][CH3:8])[CH2:4][OH:5]>CO.[Ni].O>[ClH:1].[NH2:9][C:3]([CH3:2])([CH2:6][NH:7][CH3:8])[CH2:4][OH:5]

Participants

5

Reactant 1

HCID 866655512-Methyl-3-(methylamino)-2-nitropropan-1-ol hydrochloride

Product 1

HCID 866655492-Amino-2-methyl-3-(methylamino)propan-1-ol hydrochlorideYield 163.6%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2-methyl-3-(methylamino)-2-nitropropan-1-ol hydrochloride (5.4 g) in MeOH (32 ml) was added a slurry of Raney Nickel in H2O (1.5 ml). The vessel was pressurized with H2 (450 psi) and the suspension stirred for 48 h. The mixture was filtered through Celite and concentrated in vacuo to give 7.4 g of a crude liquid, which was used directly in the next step without purification. 1H NMR (400 MHz, CDCl3) δ 1.01 (s, 3H), 2.26 (s, 3H), 2.99 (s, 2H), 3.41-3.44 (d, J=11.6 Hz, 1H), 3.48-3.51 (d, J=11.6 Hz, 1H). LRMS (ESI/APCI): 145 [M+H]+.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dd88393b34554d9c90e560c75613f695
Source dataset
uspto-grants-2014_05
Patent number
US08729112B2

Reaction notes

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