1,4-Dioxane hydrochloride → (S)-2-amino-2-(5-fluoro-2-methoxypyridin-3-yl)ethanol dihydrochloride

HRID 1426955Notes

Reaction equation

HRID 1426955 reaction equation
[Si]([O:8][CH2:9][C@@H:10]([NH:20][S@](C(C)(C)C)=O)[C:11]1[C:12]([O:18][CH3:19])=[N:13][CH:14]=[C:15]([F:17])[CH:16]=1)(C(C)(C)C)(C)C.[ClH:27].O1CCOCC1>CO>[ClH:27].[ClH:27].[NH2:20][C@@H:10]([C:11]1[C:12]([O:18][CH3:19])=[N:13][CH:14]=[C:15]([F:17])[CH:16]=1)[CH2:9][OH:8]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 86691740(S)-N-((S)-2-(tert-butyldimethylsilyloxy)-1-(5-fluoro-2-methoxypyridin-3-yl)ethyl)-2-methylpropane-2-sulfinamide

Product 1

HCID 67471079(S)-2-amino-2-(5-fluoro-2-methoxypyridin-3-yl)ethanol dihydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-N-((S)-2-(tert-butyldimethylsilyloxy)-1-(5-fluoro-2-methoxypyridin-3-yl)ethyl)-2-methylpropane-2-sulfinamide (1.40 g, 3.46 mmol) in methanol (20 mL) was added 4N HCl/dioxane (8.65 mL, 34.6 mmol). The solution was stirred at ambient temperature for 16 hours, then concentrated and dried under vacuum to afford (S)-2-amino-2-(5-fluoro-2-methoxypyridin-3-yl)ethanol dihydrochloride as a yellow oil which was used without purification, assuming 100% yield. MS (apci) m/z=186.9 (M+H).

Workup

  1. concentrationconcentrated
  2. customdried under vacuum

Sources & evidence

ORD record
ord-06295c76453646b181db4e3658e64928
Source dataset
uspto-grants-2015_01
Patent number
US08933084B2

Reaction notes

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