Hydrochloric Acid → HCID 19802059, compound

HRID 1646416Notes

Reaction equation

HRID 1646416 reaction equation
[OH:1][CH:2]([CH2:6][O:7][S:8]([C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1)(=[O:10])=[O:9])[CH2:3][C:4]#[N:5].[ClH:18].[H][H]>CO.[Pd]>[ClH:18].[OH:1][CH:2]([CH2:6][O:7][S:8]([C:11]1[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=1)(=[O:10])=[O:9])[CH2:3][CH2:4][NH2:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 142921063-Hydroxy-4-tosyloxybutanenitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 19802059HCID 19802059, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (RS)-3-hydroxy-4-(p-toluenesulfonyloxy)butyronitrile (17.0 g) in methanol (120 ml), 10 wt. % Pd on carbon (3.0 g) and conc. hydrochloric acid (30 ml) were added. The mixture was stirred in a hydrogen atmosphere of 4.0 kg/cm2 at room temperature for 20 hours. After filtrating off the catalyst, the mixture was evaporated under reduced pressure to obtain a crude product, which was purified by silica gel chromatography (Wako Gel C200, an eluent: methanol/acetone (volume ratio of 3/7) to obtain pure (RS)-3-hydroxy-4-(p-toluenesulfonyloxy)butylamine hydrochloride (18.1 g). Yield, 92 %.

Workup

  1. filtrationAfter filtrating off the catalyst
  2. customthe mixture was evaporated under reduced pressure
  3. customto obtain a crude product, which
  4. customwas purified by silica gel chromatography (Wako Gel C200

Sources & evidence

ORD record
ord-3f3d0b7f33884f65b98f2af44d09eb82
Source dataset
uspto-grants-1993_01
Patent number
US05179212

Reaction notes

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