Hydrochloric Acid → (S)-2-Amino-2-(5-fluoropyridin-2-yl)ethan-1-ol dihydrochloride
Reaction equation
[Si]([O:8][CH2:9][C@@H:10]([NH:18][S@](C(C)(C)C)=O)[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][N:12]=1)(C(C)(C)C)(C)C.[ClH:25]>CO.O>[ClH:25].[ClH:25].[NH2:18][C@@H:10]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][N:12]=1)[CH2:9][OH:8]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of (S)—N—((S)-2-(tert-butyldimethylsilyloxy)-1-(5-fluoropyridin-2-yl)ethyl)-2-methylpropane-2-sulfinamide (16 g, 43 mmol) in methanol (300 mL) was added hydrogen chloride (53 mL, 210 mmol) (4M in dioxanes) and the reaction stirred at room temperature for 2 hours. The reaction was concentrated in vacuo and the material taken up in water (200 mL) and washed with dichloromethane (200 mL) to give (S)-2-amino-2-(5-fluoropyridin-2-yl)ethanol bis-hydrochloride (9.8 g, 43 mmol) as a solution in water. The solution was used crude in the next reaction.
Workup
- concentrationThe reaction was concentrated in vacuo
- washwashed with dichloromethane (200 mL)
Sources & evidence
- ORD record
- ord-c13137eb3cb64cd1b7064449458dbc33
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08865726B2
Reaction notes
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