Hydrochloric Acid → HCID 12842605, compound

HRID 1165680Notes

Reaction equation

HRID 1165680 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 (67E, 31.08 g, 0.149 mol) was dissolved in 95% EtOH (240 mL) containing concentrated 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 acetetate salt (G. Cardillo et al., Chem. Commun. 13808, 1982), but no data was given. Attempts to duplicate the latter porcedure 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-d7ffdc9640ad466090ae816dcbd5d90c
Source dataset
uspto-grants-1990_03
Patent number
US04910218

Reaction notes

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