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Hydrochloric Acid → (1R,2S)-2-Amino-1-(4-ethylphenyl)-1-propanol

HRID 1098778
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1098778
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([OH:20])[C@@H:10]([NH:12]C(=O)OC(C)(C)C)[CH3:11])=[CH:5][CH:4]=1)[CH3:2].Cl>C(#N)C.O>[NH2:12][C@@H:10]([CH3:11])[C@@H:9]([C:6]1[CH:7]=[CH:8][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=1)[OH:20]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 59339896tert-butyl[(1S,2R)-2-(4-ethylphenyl)-2-hydroxy-1-methylethyl]carbamate

Produkt 1

HCID 28743543(1R,2S)-2-Amino-1-(4-ethylphenyl)-1-propanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

To a stirred solution of tert-butyl [(1S,2R)-2-(4-ethylphenyl)-2-hydroxy-1-methylethyl]carbamate (450 mg, 1.51 mmol) in acetonitrile (10 ml) was added aq. HCl (6 N, 3 ml), and stirring was continued for 3.5 h. Then the mixture was diluted with water (10 ml), and acetonitrile was removed in vacuo. The mixture was washed with dichloromethane (20 ml). The aqueous layer was then made alkaline (pH≈10) by addition of aq. NaOH (10 N), and extracted with dichloromethane (3×20 ml). The combined organic extracts were dried with Na2SO4, the solvent was removed in vacuo to afford white solid, 280 mg (97%).

Aufarbeitung

  1. customwas removed in vacuo
  2. washThe mixture was washed with dichloromethane (20 ml)
  3. additionby addition of aq. NaOH (10 N)
  4. extractionextracted with dichloromethane (3×20 ml)
  5. dry with materialThe combined organic extracts were dried with Na2SO4
  6. customthe solvent was removed in vacuo
  7. customto afford white solid, 280 mg (97%)

Quellen und Nachweise

ORD-Eintrag
ord-1f448a58e32f48c1b89c8cf1c6703a8c
Quelldatensatz
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08143290B2

Notizen zur Reaktion

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