Dichloromethane → n-{[(7s)-3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}-3-(7,8-dimethoxy-1,2,4,5-tetrahydro-3h-3-benzazepin-3-yl)-n-methyl-4-oxobutan-1-amine hydrochloride

HRID 657565Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 657565
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[C@@H:7]([CH2:13][NH:14][CH3:15])[CH2:6]2.[CH3:16][O:17][C:18]1[C:19]([O:35][CH3:36])=[CH:20][C:21]2NC[CH:25](C(=O)CCC=O)[CH2:24][CH2:23][C:22]=2[CH:34]=1.C(O[BH-](O[C:47](=[O:49])[CH3:48])OC(=O)C)(=O)C.[Na+].[OH-].[Na+].[Cl:53]CCl>>[ClH:53].[CH3:16][O:17][C:18]1[CH:34]=[C:22]2[C:21](=[CH:20][C:19]=1[O:35][CH3:36])[C@@H:24]([CH2:25][N:14]([CH3:15])[CH2:13][CH2:7][CH:48]([N:14]1[CH2:15][CH2:6][C:5]3[CH:4]=[C:3]([O:2][CH3:1])[C:10]([O:11][CH3:12])=[CH:9][C:8]=3[CH2:7][CH2:13]1)[CH:47]=[O:49])[CH2:23]2

Komponenten

6

Edukt 5

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 11499437(S)-1-(3,4-Dimethoxybicyclo(4.2.0)octa-1,3,5-trien-7-yl)-N-methylmethanamineHCID 876403464-(7,8-Dimethoxy-1,2,4,5-tetrahydro-3H-3-benzazepin-yl)-4-oxobutanal

Produkt 1

HCID 87640330n-{[(7s)-3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}-3-(7,8-dimethoxy-1,2,4,5-tetrahydro-3h-3-benzazepin-3-yl)-n-methyl-4-oxobutan-1-amine hydrochloride

Versuchsvorschrift

At ambient temperature, 2.53 g (12.2 mmol) of {[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}methylamine and 3.95 g (12.2 mmol/1 eq.) of the compound of Step 2 are mixed into 90 mL of dichloromethane. There are then added 3.88 g (18.3 mmol/1.5 eq.) of sodium triacetoxyborohydride and stirring is carried out at ambient temperature for 4 hours. There are then added 60 mL of 1N aqueous sodium hydroxide solution, followed by extraction twice with 150 mL of ethyl acetate. The combined organic phases are washed with 100 mL of water and then with 100 mL of saturated aqueous sodium chloride solution and are then dried over magnesium sulphate. After filtration and concentration, the residue is chromatographed over 300 g of silica (eluant:dichloromethane/ethanol/ammonia: 97/3/0.3) to yield the desired product in the form of the base. The latter is dissolved in 13 mL of isopropanol, converted into a salt using 0.67 mL of 4.8N ethanolic HCl and then recrystallised from 25 mL of ethyl acetate to yield the expected product.

Aufarbeitung

  1. extractionfollowed by extraction twice with 150 mL of ethyl acetate
  2. washThe combined organic phases are washed with 100 mL of water
  3. dry with materialwith 100 mL of saturated aqueous sodium chloride solution and are then dried over magnesium sulphate
  4. filtrationAfter filtration and concentration
  5. customthe residue is chromatographed over 300 g of silica (eluant:dichloromethane/ethanol/ammonia: 97/3/0.3)

Quellen und Nachweise

ORD-Eintrag
ord-0887c5600aaa4085a7423204714fd254
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08076325B2

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