Trifluoroacetic acid → (S)-2-amino-4-(5-trifluoromethyl-pyridin-2-yloxy)-butan-1-ol
Reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[C@@H:19]([CH2:20][CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][N:24]=2)[CH2:18][O:17]C1(C)C)=O)(C)(C)C.[OH-].[Na+]>O.C(#N)C.C(OCC)(=O)C>[NH2:15][C@@H:19]([CH2:20][CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:30])[F:31])=[CH:25][N:24]=1)[CH2:18][OH:17]Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 80 °C
Procedure
To a solution of trifluoroacetic acid (0.23 ml) in water (9 ml) was added dropwise a solution of (S)-2,2-dimethyl-4-[2-(5-trifluoromethyl-pyridin-2-yloxy)-ethyl]-oxazolidine-3-carboxylic acid tert-butyl ester (390 mg) in acetonitrile (1.5 ml). The mixture was heated for 90 min at 80° C. with stirring. The mixture was then cooled to room temperature and made basic by addition of 2 M aq. sodium hydroxide solution, then diluted with ethyl acetate and washed sequentially with water and with saturated brine. The organic phase was separated, dried over sodium sulphate and concentrated in vacuo to give (S)-2-amino-4-(5-trifluoromethyl-pyridin-2-yloxy)-butan-1-ol (284 mg, quant.) as a yellow oil. MS (ISP): 251.2 ([M+H]+).
Workup
- temperatureThe mixture was then cooled to room temperature
- washwashed sequentially with water and with saturated brine
- customThe organic phase was separated
- dry with materialdried over sodium sulphate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-e8cc73cfb5fb44beb5b36558cb9865a1
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08357712B2
Reaction notes
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