Hydrochloric Acid → [(4aR,6R,8aS)-2-amino-8a-(2-fluorophenyl)-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-6-yl]methanol

HRID 217991Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 217991
Cl.C([O:9][CH2:10][C@@H:11]1[O:20][CH2:19][C@@:18]2([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])[C@H:13]([CH2:14][S:15][C:16]([NH2:28])=[N:17]2)[CH2:12]1)C1C=CC=CC=1.[OH-].[Na+]>>[NH2:28][C:16]1[S:15][CH2:14][C@H:13]2[C@:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])([CH2:19][O:20][C@@H:11]([CH2:10][OH:9])[CH2:12]2)[N:17]=1

Komponenten

4

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59281170(4aR,6R,8aS)-6-benzyloxymethyl-8a-(2-fluorophenyl)-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-2-ylamine

Produkt 1

HCID 58406040[(4aR,6R,8aS)-2-amino-8a-(2-fluorophenyl)-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-6-yl]methanolAusbeute 92,1 %

Versuchsvorschrift

Concentrated hydrochloric acid (25.2 ml) was added to (4aR,6R,8aS)-6-benzyloxymethyl-8a-(2-fluorophenyl)-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-2-ylamine (1.26 g), and the mixture was heated under reflux for two hours. After cooling the reaction solution to room temperature, the reaction mixture was poured into ice. The mixture was neutralized with 5 N sodium hydroxide, and the aqueous layer was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residual solid was washed with a mixed solvent of heptane and ether to obtain the title compound (890 mg).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for two hours
  3. additionthe reaction mixture was poured into ice
  4. extractionthe aqueous layer was extracted with dichloromethane
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. washthe residual solid was washed with a mixed solvent of heptane and ether

Quellen und Nachweise

ORD-Eintrag
ord-4925a051a39b402bb48213693ce947fc
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198269B2

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