StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Hydrochloric Acid → [1-(4-Fluoro-phenyl)-4-hydroxy-cyclohexyl]-carbamic acid benzyl ester

HRID 2370297
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2370297
[CH2:1]([O:8][C:9](=[O:25])[NH:10][C:11]1([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].O.Cl>C1COCC1>[CH2:1]([O:8][C:9](=[O:25])[NH:10][C:11]1([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 59226032[1-(4-Fluoro-phenyl)-4-oxo-cyclohexyl]-carbamic acid benzyl ester

Produkt 1

HCID 59226075[1-(4-Fluoro-phenyl)-4-hydroxy-cyclohexyl]-carbamic acid benzyl esterAusbeute 91,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

1.5 g of [1-(4-Fluoro-phenyl)-4-oxo-cyclohexyl]-carbamic acid benzyl ester (77) were dissolved in 30 mL of dry THF and 182 mg of sodium borohydride were added. When conversion was complete, the mixture was poured into 15 mL of water. pH was adjusted to 2 by addition of 2N HCl and the aqueous layer was extracted with ethyl acetate. The combined organic layer was extracted with brine, dried over magnesium sulfate and evaporated to dryness to give 1.38 g of the desired product as a mixture of cis and trans isomers, the cis isomer (referring to the position of alcohol and Z-amine) being the major one. Rt=2.20 min (Method E). Detected mass: 344.2 (M+H+).

Aufarbeitung

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. extractionThe combined organic layer was extracted with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-644bf06191cc4b31b01dc811659c6e09
Quelldatensatz
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08710077B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion