Benzyl Bromide → (4bS,8R,8aS,9aR,10S,13aR,13bR)-1-benzyloxy-10-tert-butyl-7-cyclopropylmethyl-5,6,7,8,9,9a,10,13b-octahydro-10-methyl-8a,13a-ethano-4,8-methanobenzofuro[3,2-e][1,3]dioxino[4,5-g]isoquinoline

HRID 629832Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 629832
[C:1]([C@:5]1([CH3:34])[C@@H:18]2[C@@:9]3([CH2:20][CH2:19][C@:16]4([CH2:17]2)[C@@:11]25[C:27]6[C:22](=[CH:23][CH:24]=[C:25]([OH:29])[C:26]=6[O:28][C@@H:10]32)[CH2:21][C@H:15]4[N:14]([CH2:30][CH:31]2[CH2:33][CH2:32]2)[CH2:13][CH2:12]5)[O:8][CH2:7][O:6]1)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH2:41](Br)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>CC(C)=O>[CH2:41]([O:29][C:25]1[C:26]2[O:28][C@H:10]3[C@@:9]45[CH2:20][CH2:19][C@:16]6([CH2:17][C@@H:18]4[C@:5]([C:1]([CH3:4])([CH3:2])[CH3:3])([CH3:34])[O:6][CH2:7][O:8]5)[C@@:11]43[CH2:12][CH2:13][N:14]([CH2:30][CH:31]3[CH2:32][CH2:33]3)[C@@H:15]6[CH2:21][C:22]([C:27]=24)=[CH:23][CH:24]=1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 73211769(4bS,8R,8aS,9aR,10S,13aR,13bR)-10-tert-butyl-7-cyclopropylmethyl-5,6,7,8,9,9a,10,13b-octahydro-10-methyl-8a,13a-ethano-4,8-methanobenzofuro[3,2-e][1,3]dioxino[4,5-g]isoquinolin-1-ol

Produkt 1

HCID 121278739(4bS,8R,8aS,9aR,10S,13aR,13bR)-1-benzyloxy-10-tert-butyl-7-cyclopropylmethyl-5,6,7,8,9,9a,10,13b-octahydro-10-methyl-8a,13a-ethano-4,8-methanobenzofuro[3,2-e][1,3]dioxino[4,5-g]isoquinolineAusbeute 55,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a suspension of compound 3 (1.0 g, 2.15 mMol) and K2CO3 (0.88 g, 6.45 mMol) in acetone (10 ml) was added benzyl bromide (0.31 mL, 2.15 mMol). The resulting suspension was stirred at ambient temperature for 24 h. All volatiles were removed by vacuum distillation. The crude product was purified by column chromatography on silica to give 0.66 g of the title compound 7 (54.5% yield) in a purity of 96.9% as a white solid.

Aufarbeitung

  1. customAll volatiles were removed by vacuum distillation
  2. customThe crude product was purified by column chromatography on silica

Quellen und Nachweise

ORD-Eintrag
ord-6a5f7b5cc5af4089a738361e7a24b2ca
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09315514B2

Notizen zur Reaktion

Wird geladen…