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Sodium hydride → (r)-(+)-5,11-Dihydro-5-[1-(4-fluorophenethyl)-2-pyrrolidinyl methyl]dibenzo[b,e][1,4]oxazepine

HRID 365315
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 365315
[H-].[Na+].[CH:3]1[C:13]2[CH2:12][O:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[NH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.Cl[C@H:19]1[CH2:24][CH2:23][CH2:22][N:21]([CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[CH2:20]1>CS(C)=O>[F:33][C:30]1[CH:29]=[CH:28][C:27]([CH2:26][CH2:25][N:21]2[CH2:22][CH2:23][CH2:24][C@@H:20]2[CH2:19][N:8]2[C:7]3[CH:6]=[CH:5][CH:4]=[CH:3][C:13]=3[CH2:12][O:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]2=3)=[CH:32][CH:31]=1
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Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 110847985,11-Dihydrodibenzo[b,e][1,4]oxazepineHCID 15481944(S)-(+)-3-chloro-1-(4-fluorophenethyl)piperidine

Produkt 1

HCID 15481929(r)-(+)-5,11-Dihydro-5-[1-(4-fluorophenethyl)-2-pyrrolidinyl methyl]dibenzo[b,e][1,4]oxazepineAusbeute 45,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679
Dimethyl Sulfoxide
Lösungsmittel
2×

Versuchsvorschrift

Four-hundred milligrams (9.9 mmols) of 60% sodium hydride were washed with petroleum ether, and then suspended in 40 ml of dimethyl sulfoxide. To the suspension were added 1.5 g (7.6 mmols) of 5,11-dihydrodibenzo[b,e][1,4]oxazepine. The mixture was stirred in a nitrogen atmosphere at room temperature for 1 hour. To this reaction solution was added dropwise a solution of 2.2 g (9.1 mmols) of (S)-(+)-3-chloro-1-(4-fluorophenethyl)piperidine [[α]D25 =+9.5° (c=1.0, ethano l)] in 10 ml of dimethyl sulfoxide, and the mixed solution was stirred at room temperature for 4 days. The reaction solution was poured into ice water, and extracted with ethyl acetate. The organic layer was washed with water and with a saturated aqueous solution of sodium chloride in this order, and dried. Subsequently, the solvent was distilled off under reduced pressure. The resulting residue was subjected to column chromatography, and eluted with a mixed solvent of ethyl acetate and hexane at a ratio of 1:2. This mixed solvent was distilled off under reduced pressure to give 1.4 g of (R)-(+)-5,11-dihydro-5-[1-(4-fluorophenethyl)-2-pyrrolidinylmethyl]dibenzo[b,e][1,4]oxazepine as a pale yellow oil in a yield of 44%.

Aufarbeitung

  1. stirringthe mixed solution was stirred at room temperature for 4 days
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and with a saturated aqueous solution of sodium chloride in this order
  4. customdried
  5. distillationSubsequently, the solvent was distilled off under reduced pressure
  6. washeluted with a mixed solvent of ethyl acetate and hexane at a ratio of 1:2
  7. distillationThis mixed solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8061c78a599541838bb9d4cf31be0de3
Quelldatensatz
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06127361

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