Acetic Acid → 1-(4-chlorophenethyl)-5-cyclopropyl-8-methoxy-2,3,5,6-tetrahydrobenzo[b][1,5]diazocin-4(1H)-one

HRID 1614896Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1614896
[CH:1]1([N:4]2[C:11](=[O:12])[CH2:10][CH2:9][NH:8][C:7]3[CH:13]=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:6]=3[CH2:5]2)[CH2:3][CH2:2]1.C(O)(=O)C.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH:31]=O)=[CH:26][CH:25]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClC(Cl)C>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][N:8]2[CH2:9][CH2:10][C:11](=[O:12])[N:4]([CH:1]3[CH2:2][CH2:3]3)[CH2:5][C:6]3[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:7]2=3)=[CH:26][CH:25]=1

Komponenten

7

Edukt 5

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 114125022-(4-Chlorophenyl)acetaldehydeHCID 529398795-cyclopropyl-8-methoxy-2,3,5,6-tetrahydrobenzo[b][1,5]diazocin-4(1H)-one

Produkt 1

HCID 529398801-(4-chlorophenethyl)-5-cyclopropyl-8-methoxy-2,3,5,6-tetrahydrobenzo[b][1,5]diazocin-4(1H)-oneAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

To a solution of 5-cyclopropyl-8-methoxy-2,3,5,6-tetrahydrobenzo[b][1,5]diazocin-4(1H)-one (50.0 mg, 0.203 mmol) from Example 1 in dichloroethane (2 ml) at 0° C. was added acetic acid (0.035 ml, 0.609 mmol), 2-(4-chlorophenyl)acetaldehyde (47.0 mg, 0.304 mmol) prepared as above and sodium triacetoxyborohydride (129.0 mg, 0.609 mmol). The mixture was stirred overnight at room temperature and then sodium bicarbonate was added followed by extraction with dichloromethane. The organic phases were dried over sodium sulfate, filtered and concentrated. Preparative thin layer chromatography (pentane/ethyl acetate: 1/1) of the obtained residue gave the desired compound as a yellow oil (59 mg, 76%).

Aufarbeitung

  1. extractionfollowed by extraction with dichloromethane
  2. dry with materialThe organic phases were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-01ffbf3cc2d84144840891b10a37a4b0
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765728B2

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