Sodium Hydroxide → 7-({2-[benzyl(methyl)amino]ethoxy}methyl)-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylic acid

HRID 1669493Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1669493
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:28]([O:30]C)=[O:29])=[CH:12][C:13]=3[N:14]3[C:21]=2[C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[O:18][CH2:17][CH:16]([CH2:26][OH:27])[CH2:15]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].[Cl-].[CH2:35]([NH+:42]([CH3:46])[CH2:43][CH2:44]Cl)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:35]([N:42]([CH3:46])[CH2:43][CH2:44][O:27][CH2:26][CH:16]1[CH2:15][N:14]2[C:13]3[CH:12]=[C:11]([C:28]([OH:30])=[O:29])[CH:10]=[CH:9][C:8]=3[C:7]([CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[C:21]2[C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[O:18][CH2:17]1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 31967Benzylamine, N-(2-chloroethyl)-N-methyl-, hydrochlorideHCID 66674539HCID 66674539, Verbindung

Produkt 1

HCID 866279097-({2-[benzyl(methyl)amino]ethoxy}methyl)-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A solution of (+)-methyl 14-cyclohexyl-7-(hydroxymethyl)-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (second eluting isomer) in toluene (0.04 M) was treated with 30% w/v NaOH (10 eq) and tetrabutylammonium bromide (0.25 eq) followed by N-benzyl-2-chloro-N-methylethanaminium chloride (prepared as described in example 7 step 1) (2.5 eq). The resulting solution was stirred at 65° C. for 18 h. Toluene was removed in vacuo, the residue was taken up in EtOAc and washed with 1N HCl (aq) and brine before drying (Na2SO4), filtering and concentrating in vacuo to afford the product as an oil that was used without further purification. (ES+) m/z 553 (M+H)+.

Aufarbeitung

  1. customToluene was removed in vacuo
  2. washwashed with 1N HCl (aq) and brine
  3. dry with materialbefore drying (Na2SO4)
  4. filtrationfiltering
  5. concentrationconcentrating in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-98a6c263c3fd43759dce62a44175fd1d
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989438B2

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