Hydrochloric Acid → (S)-2-amino-4-[1-(4-chloro-phenyl)-cyclopropyl]-butan-1-ol

HRID 1807915ノート

反応式

HRID 1807915 の反応式
C(OC([N:8]1[C@@H:12]([CH2:13][CH2:14][C:15]2([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)[CH2:17][CH2:16]2)[CH2:11][O:10]C1(C)C)=O)(C)(C)C.Cl>C(O)C>[NH2:8][C@@H:12]([CH2:13][CH2:14][C:15]1([C:18]2[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=2)[CH2:17][CH2:16]1)[CH2:11][OH:10]

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 67177641(S)-4-{2-[1-(4-chloro-phenyl)-cyclopropyl]-ethyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

生成物 1

HCID 67179178(S)-2-amino-4-[1-(4-chloro-phenyl)-cyclopropyl]-butan-1-ol収率 85.6%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To (S)-4-{2-[1-(4-chloro-phenyl)-cyclopropyl]-ethyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (0.5 g) was added under an argon atmosphere 5.5 M HCl solution in ethanol (2 ml). The mixture was stirred for 16 h. The mixture was concentrated. The residue was dissolved in dichloromethane and an excess of ammonia in methanol and some silica gel was added. The solvents were evaporated and the crude product was purified by column chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: dichloromethane/methanol=90:10) to give (S)-2-amino-4-[1-(4-chloro-phenyl)-cyclopropyl]-butan-1-ol (0.27 g) as a white solid. MS (ISP): 240.2 ([M+H]+)).

後処理

  1. concentrationThe mixture was concentrated
  2. dissolutionThe residue was dissolved in dichloromethane
  3. additionan excess of ammonia in methanol and some silica gel was added
  4. customThe solvents were evaporated
  5. customthe crude product was purified by column chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: dichloromethane/methanol=90:10)

出典と根拠

ORDレコード
ord-2444c4db5c6547daaba50240d58af442
出典データセット
uspto-grants-2013_01
特許番号
US08357712B2

反応ノート

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