Hydrochloride methanol → N-[4-[(1R)-1-aminoethyl]-2-(hydroxymethyl)phenyl]methanesulfonamide hydrochloride

HRID 230593Notes

Reaction equation

HRID 230593 reaction equation
C([S@]([NH:7][C@@H:8]([C:10]1[CH:15]=[CH:14][C:13]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])=[C:12]([CH2:21][OH:22])[CH:11]=1)[CH3:9])=O)(C)(C)C.[ClH:23].CO>CO>[ClH:23].[NH2:7][C@@H:8]([C:10]1[CH:15]=[CH:14][C:13]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])=[C:12]([CH2:21][OH:22])[CH:11]=1)[CH3:9]

Participants

4

Reactant 2

HCID 21893726Hydrochloride methanolHCID 68714531N-[4-((1R)-1-{[(R)-tert-butylsulfinyl]amino}ethyl)-2-(hydroxymethyl)phenyl]methanesulfonamide

Product 1

HCID 68804307N-[4-[(1R)-1-aminoethyl]-2-(hydroxymethyl)phenyl]methanesulfonamide hydrochlorideYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-[4-((1R)-1-{[(R)-tert-butylsulfinyl]amino}ethyl)-2-(hydroxymethyl)phenyl]methanesulfonamide (3.6 g,10 mmol) in methanol (30 ml) was added hydrogenchloride-methanol solution (30 ml). The solution was stirred at room temperature for 30 minutes and then concentrated under reduced pressure. The given residue was recrystallized from methanol-diethyl ether. The precipitate was then filtered, washed with diethyl ether and collected to furnish 2.5 g (87% yield) of the title compound as a yellow oil.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe given residue was recrystallized from methanol-diethyl ether
  3. filtrationThe precipitate was then filtered
  4. washwashed with diethyl ether
  5. customcollected

Sources & evidence

ORD record
ord-89a7101265e44a5d8bed3465caa43f72
Source dataset
uspto-grants-2009_07
Patent number
US07566739B2

Reaction notes

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