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

HRID 1026130Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1026130
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]

Komponenten

4

Edukt 2

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

Produkt 1

HCID 67179178(S)-2-amino-4-[1-(4-chloro-phenyl)-cyclopropyl]-butan-1-olAusbeute 85,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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]+)).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-99a6f3b2bc0e4c24ab82908cd2c5ecc7
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08729113B2

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