Methane → (S)-5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-ylamine hydrochloride

HRID 863062Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 863062
O.[OH-].[Li+].[F:4][C:5]1[CH:14]=[C:13]([F:15])[CH:12]=[C:11]2[C:6]=1[CH2:7][CH2:8][C@H:9]([NH:16]C(=O)C(F)(F)F)[CH2:10]2.[ClH:23].C>CO.O>[ClH:23].[F:4][C:5]1[CH:14]=[C:13]([F:15])[CH:12]=[C:11]2[C:6]=1[CH2:7][CH2:8][C@H:9]([NH2:16])[CH2:10]2

Komponenten

7

Edukt 4

HCID 297MethaneHCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 15290004(S)-5,7-difluoro-2-[(trifluoroacetyl)amino]-1,2,3,4-tetrahydronaphthalene

Produkt 1

HCID 66789737(S)-5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-ylamine hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel3×HCID 962WaterLösungsmittel2×

Versuchsvorschrift

Lithium hydroxide monohydrate (7.8 g, 0.2 mol) was added to a solution of (S)-5,7-difluoro-2-[(trifluoroacetyl)amino]-1,2,3,4-tetrahydronaphthalene (20.8 g, 74.5 mmol) in 187 mL of methanol and 21 mL of water. The mixture was stirred at reflux for 30 minutes and diluted with 200 mL of methanol. The diluted mixture then was combined with 60 mL of water, 24.8 mL of concentrated hydrochloric acid and 4.2 g of activated carbon, Darco®. The mixture was stirred for 30 minutes and then filtered through Celite. The filtrate was distilled until the head temperature reached 75° C. The remaining mixture was allowed to cool and let stand for approximately 60 hours. The mixture then was cooled in an ice bath giving a crystalline material. The material was isolated by filtration and the filter residue was washed with water. Drying to constant weight in vacuo at room temperature under a nitrogen stream gave (S)-5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-ylamine hydrochloride (14.8 g, 67.6 mol), m.p.>280° C. [α]D -66.2° (c=0.162, CH3OH).

Aufarbeitung

  1. temperatureat reflux for 30 minutes
  2. stirringThe mixture was stirred for 30 minutes
  3. filtrationfiltered through Celite
  4. distillationThe filtrate was distilled until the head temperature
  5. customreached 75° C
  6. temperatureto cool
  7. temperatureThe mixture then was cooled in an ice bath
  8. customgiving a crystalline material
  9. customThe material was isolated by filtration
  10. washthe filter residue was washed with water
  11. customDrying to constant weight in vacuo at room temperature under a nitrogen stream

Quellen und Nachweise

ORD-Eintrag
ord-66e8919b5292486f8af217bf61fe84de
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05719280

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