Acetic Acid → HCID 14371630, Verbindung

HRID 1464006Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1464006
[CH3:1][O:2][C:3]1[C:4]([Cl:21])=[CH:5][C:6]2[CH:12]=[CH:11][NH:10][C@@H:9]3[CH2:13][C:14]4[C:19]([C@H:8]3[C:7]=2[CH:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=4.C([BH3-])#N.[Na+].C(O)(=O)C>C(O)C>[CH3:1][O:2][C:3]1[C:4]([Cl:21])=[CH:5][C:6]2[CH2:12][CH2:11][NH:10][C@@H:9]3[CH2:13][C:14]4[C:19]([C@H:8]3[C:7]=2[CH:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=4

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 14371625HCID 14371625, Verbindung

Produkt 1

HCID 14371630HCID 14371630, VerbindungAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

The crude Compound N from step D was dissolved in 20 mL absolute ethanol and treated with 0.12 grams (1.91 mmol) sodium cyanoborohydride. To this was added 0.108 mL glacial acetic acid, and the mixture was stirred at room temperature for 3 hours. The reaction was quenched with 10 mL 1M HCl and stirred for 30 minutes. The reaction was made basic with 30% NaOH and extracted into 250 mL ethyl actetate. The organic layer was dried (MgSO4) and evaporated to give 350 mg (53%) of trans-5,6,7,7a,8,12b-hexahydro-2-methoxy-3-chlorobenz[d]indeno[2,1-b]azepine (Compound P) as an oil, 200 MHz NMR (CDCl3) d 3.60-3.85(m,3H), 3.10-3.40(m,4H), 3.71(s,3H), 4.54(d,1H,J=8 Hz), 7.07(s,1H), 7.16(s,1H), 7.20-7.40(m,4H).

Aufarbeitung

  1. customThe reaction was quenched with 10 mL 1M HCl
  2. stirringstirred for 30 minutes
  3. extractionextracted into 250 mL ethyl actetate
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-955988b28661424babf52ac658a2ad04
Quelldatensatz
uspto-grants-1994_04
Patentnummer
US05302716

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