Triphenylphosphine → (1E,3aR,4E,7aS)-4-(bromomethylene)-1-ethylidene-octahydro-7a-methyl-1H-indene

HRID 1922635Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1922635
[Br:1]/[CH:2]=[C:3]1\[CH2:4][CH2:5][CH2:6][C@@:7]2([CH3:15])[C@H:11]\1[CH2:10][CH2:9][C@@H:8]2[C@@H:12](O)[CH3:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(N=NC(OCC)=O)=O)C>O1CCCC1>[Br:1]/[CH:2]=[C:3]1/[C@H:11]2[C@:7]([CH3:15])([CH2:6][CH2:5][CH2:4]/1)/[C:8](=[CH:12]/[CH3:13])/[CH2:9][CH2:10]2

Komponenten

5

Edukt 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 59456539(S)-1-{(E,3S,3aS,7aR)-7-(bromomethylene)-octahydro-3a-methyl-1H-indene-3-yl}ethanol2×

Produkt 1

HCID 59456521(1E,3aR,4E,7aS)-4-(bromomethylene)-1-ethylidene-octahydro-7a-methyl-1H-indeneAusbeute 44,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Under a nitrogen atmosphere, a solution of (S)-1-{(E,3S,3aS,7aR)-7-(bromomethylene)-octahydro-3a-methyl-1H-indene-3-yl}ethanol (Compound 18: 52.4 mg, 0.1918 mmol) and triphenylphosphine (126 mg, 0.4795 mmol) in tetrahydrofuran (0.3 ml) was cooled in an ice bath, and azodicarboxylic acid diethyl ester (2.2 M in toluene, 223.4 μl, 0.4915 mmol) was added dropwise thereto. The reaction mixture was stirred in the ice bath for 10 minutes and at room temperature for 21 hours, and then evaporated under reduced pressure. The obtained crude product was purified by flash column chromatography to obtain (1E,3aR,4E,7aS)-4-(bromomethylene)-1-ethylidene-octahydro-7a-methyl-1H-indene (21.8 mg, 44.6%).

Aufarbeitung

  1. customevaporated under reduced pressure
  2. customThe obtained crude product
  3. customwas purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-45d9ab5d91d64b2ba5c527c086942bbe
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173824B2

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