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

HRID 885180노트

반응식

HRID 885180 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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]+)).

후처리

  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)

출처 및 근거

ORD 기록
ord-4f0254fa2fe543c1940a40c30698dc9c
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08242153B2

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