1,1-Dicyclopropyl-2-dibenzylamino-ethanol → 2-Amino-1,1-dicyclopropylethan-1-ol

HRID 1865893Notes

Reaction equation

HRID 1865893 reaction equation
[CH:1]1([C:4]([CH:22]2[CH2:24][CH2:23]2)([OH:21])[CH2:5][N:6](CC2C=CC=CC=2)CC2C=CC=CC=2)[CH2:3][CH2:2]1.[H][H]>CO.[OH-].[OH-].[Pd+2].C>[NH2:6][CH2:5][C:4]([CH:22]1[CH2:24][CH2:23]1)([CH:1]1[CH2:3][CH2:2]1)[OH:21]

Participants

5

Reactant 2

HCID 687982851,1-Dicyclopropyl-2-dibenzylamino-ethanolHCID 178418361HCID 178418361, compound

Product 1

HCID 552845292-Amino-1,1-dicyclopropylethan-1-olYield 81.4%

Reagents, catalysts & solvents 2

HCID 86583698HCID 86583698, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 0.28 g 1,1-dicyclopropyl-2-dibenzylamino-ethanol (0.00087 mol) in 10 ml methanol was added 0.060 g Pd(OH)2/charcoal (Fluka 7663; 20%) and the mixture was hydrogenated under 8 bar hydrogen pressure at 60° C. for 2 hours. The catalyst was removed by filtration and the mother liquor was concentrated and the residue was purified by chromatography on silicagel with MeCl2/MeOH/NH3 90:10:1 to yield 0.10 g (81% yield) of the title compound as colorless oil. 1H-NMR (CDCl3 300 MHz, δ ppm) 0.28-0.45 (m, 8H); 0.71-0.78 (m, 2H); 2.77 (s, 2H) ppm.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe mother liquor was concentrated
  3. customthe residue was purified by chromatography on silicagel with MeCl2/MeOH/NH3 90:10:1

Sources & evidence

ORD record
ord-5338c02ab66f43eab5e494373880c204
Source dataset
uspto-grants-2009_12
Patent number
US07629346B2

Reaction notes

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