Hydrochloric Acid → (1R,2S)-1-(3,4-difluorophenyl)-2-[[(1R)-2-hydroxy-1-methylethyl]amino]propanol

HRID 265235ノート

反応式

HRID 265235 の反応式
Br.[F:2][C:3]1[CH:4]=[C:5]([C@:10]2([OH:18])[O:15][CH2:14][C@@H:13]([CH3:16])[NH:12][C@H:11]2[CH3:17])[CH:6]=[CH:7][C:8]=1[F:9].C(O)C.O.[BH4-].[Na+].Cl>O>[F:2][C:3]1[CH:4]=[C:5]([C@@H:10]([OH:18])[C@@H:11]([NH:12][C@H:13]([CH3:16])[CH2:14][OH:15])[CH3:17])[CH:6]=[CH:7][C:8]=1[F:9]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 19096565Water ethanolHCID 67706270(2S, 3S, 5R)-2-(3,4difluorophenyl)-3,5-dimethyl-2-morpholinol hydrobromide

生成物 1

HCID 54225803(1R,2S)-1-(3,4-difluorophenyl)-2-[[(1R)-2-hydroxy-1-methylethyl]amino]propanol

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a solution of (2S,3S,5R)-2-(3,4-difluorophenyl)-3,5-dimethyl-2-morpholinol hydrobromide (25.4 g, 0.078 mole) in 50--50 ethanol-water (300 ml) was added a solution of sodium borohydride (11.9 g, 0.31 mole) in water (120 ml) at 0° C. The resulting mixture was stirred for 16 hours at room temperature. The reaction mixture was treated with concentrated hydrochloric acid and concentrated under reduced pressure. The residue was dissolved in water, basified (40% aqueous sodium hydroxide), and extracted with dichloromethane. The organic layers were combined, washed with brine and dried (potassium carbonate) to give a solution of (1R,2S)-1-(3,4-difluorophenyl)-2-[[(1R)-2-hydroxy-1-methylethyl]amino]propanol in dichlomethane (500 ml). 50 ml of the solution was concentrated under reduced pressure to yield 1.9 g of the free base as a white solid. The free base was dissolved in diethyl ether and treated with ethereal hydrogen chloride. The hydrochloride salt was recrystallized from ethanol-diethyl ether mixtures to give 1.1 g of (1R,2S)-1-(3,4-difluorophenyl)-2-[[(1R)-2-hydroxy-1-methylethyl]amino]propanol hydrochloride as a white solid. m.p. 116°-117° C.

後処理

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in water
  3. extractionextracted with dichloromethane
  4. washwashed with brine
  5. dry with materialdried (potassium carbonate)

出典と根拠

ORDレコード
ord-03490d7d38a0454e86827525a094716d
出典データセット
uspto-grants-1997_07
特許番号
US05648347

反応ノート

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