Hydrochloric Acid → HCID 19802057, compound

HRID 1646417Notes

Reaction equation

HRID 1646417 reaction equation
[OH:1][CH:2]([CH2:6][O:7][S:8]([CH3:11])(=[O:10])=[O:9])[CH2:3][C:4]#[N:5].[ClH:12].[H][H]>CO.[Pd]>[ClH:12].[OH:1][CH:2]([CH2:6][O:7][S:8]([CH3:11])(=[O:10])=[O:9])[CH2:3][CH2:4][NH2:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 15037030HCID 15037030, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19802057HCID 19802057, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (RS)-3-hydroxy-4-(methanesulfonyloxy)butyronitrile (14.6 g) in methanol (60 ml), 10 wt. % Pd on carbon (2.5 g) and conc. hydrochloric acid (15 ml) were added. The mixture was stirred in a hydrogen atmosphere of 4.0 kg/cm2 at room temperature for 8 hours. After filtering 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 1/9) to obtain pure (RS)-3-hydroxy-4-(methanesulfonyloxy)butylamine hydrochloride (15.4 g). Yield, 85 %.

Workup

  1. filtrationAfter filtering 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-62f4fe002bd94cd78cdcaf8644865748
Source dataset
uspto-grants-1993_01
Patent number
US05179212

Reaction notes

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