Hydrochloric Acid → HCID 12842605, compound

HRID 1193729Notes

Reaction equation

HRID 1193729 reaction equation
C([NH:8][C:9]([CH3:15])([CH2:12][CH2:13][OH:14])[CH2:10][OH:11])C1C=CC=CC=1.[ClH:16]>CCO.[Pd]>[ClH:16].[NH2:8][C:9]([CH3:15])([CH2:12][CH2:13][OH:14])[CH2:10][OH:11]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 13375422HCID 13375422, compound

Product 1

HCID 12842605HCID 12842605, compoundYield 90.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-Benzylamino-2-methyl-1,4-butanediol (12E, 31.08 g, 0.149 mol) was dissolved in 95% EtOH (240 mL) containing conc. HCl (21 mL, 0.25 mol) and 5% Pd/C (10.0 g) and reduced in a Parr apparatus at 40 psi over 37 h at RT. The catalyst was then removed by filtration and the solvent removed by rotary evaporation (bath at 60°) to give 20.91 g of 2-amino-2-methyl-1,4-butanediol hydrochloride (90.2%) as a clear, thick, colorless oil with acceptable NMR and mass spectra. It was used without further purification. This compound has been reported as its acetate salt (G. Cardillo et al., Chem. Commun. 1308, 1982), but no data was given. Attempts to duplicate the latter procedure were unsuccessful.

Workup

  1. customThe catalyst was then removed by filtration
  2. customthe solvent removed by rotary evaporation (bath at 60°)

Sources & evidence

ORD record
ord-d770135a6d904d6080fd276e0804a6cd
Source dataset
uspto-grants-1989_03
Patent number
US04810727

Reaction notes

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