Trifluoroacetic acid → (S)-2-amino-4-(5-trifluoromethyl-pyridin-2-yloxy)-butan-1-ol

HRID 1026153ノート

反応式

HRID 1026153 の反応式
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]

参加物

7

反応物 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 59173205(S)-2,2-dimethyl-4-[2-(5-trifluoromethyl-pyridin-2-yloxy)-ethyl]-oxazolidine-3-carboxylic acid tert-butyl ester

生成物 1

HCID 59173196(S)-2-amino-4-(5-trifluoromethyl-pyridin-2-yloxy)-butan-1-ol収率 113.6%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

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]+).

後処理

  1. temperatureThe mixture was then cooled to room temperature
  2. washwashed sequentially with water and with saturated brine
  3. customThe organic phase was separated
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-92c2d4d88f46446589097fa708d82c69
出典データセット
uspto-grants-2014_05
特許番号
US08729113B2

反応ノート

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