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Diisobutylaluminum hydride → (E)-1-[2-[4-[3-[4-[3-(1-Pyrrolidinyl)-1-propenyl]benzyl]benzo[b]thiophen-2-yl]phenoxy]ethyl]pyrrolidine Dioxalate

HRID 1070329
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Reaktionsgleichung

Reaktionsgleichung von HRID 1070329
[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[C:7]([OH:12])(=[O:11])[C:8]([OH:10])=[O:9].[N:13]1([CH2:18][C:19]#[C:20][C:21]2[CH:50]=[CH:49][C:24]([CH2:25][C:26]3[C:27]4[CH:48]=[CH:47][CH:46]=[CH:45][C:28]=4[S:29][C:30]=3[C:31]3[CH:44]=[CH:43][C:34]([O:35][CH2:36][CH2:37][N:38]4[CH2:42][CH2:41][CH2:40][CH2:39]4)=[CH:33][CH:32]=3)=[CH:23][CH:22]=2)[CH2:17][CH2:16][CH2:15][CH2:14]1.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[C:7]([OH:12])(=[O:11])[C:8]([OH:10])=[O:9].[N:13]1([CH2:18]/[CH:19]=[CH:20]/[C:21]2[CH:22]=[CH:23][C:24]([CH2:25][C:26]3[C:27]4[CH:48]=[CH:47][CH:46]=[CH:45][C:28]=4[S:29][C:30]=3[C:31]3[CH:44]=[CH:43][C:34]([O:35][CH2:36][CH2:37][N:38]4[CH2:39][CH2:40][CH2:41][CH2:42]4)=[CH:33][CH:32]=3)=[CH:49][CH:50]=2)[CH2:17][CH2:16][CH2:15][CH2:14]1
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Komponenten

4

Edukt 2

HCID 14487Diisobutylaluminum hydrideHCID 867570901-[2-[4-[3-[4-[3-(1-Pyrrolidinyl)-1-propynyl]benzyl]benzo[b]thiophen-2-yl]phenoxy]ethyl]pyrrolidine Dioxalate

Produkt 1

HCID 86757091(E)-1-[2-[4-[3-[4-[3-(1-Pyrrolidinyl)-1-propenyl]benzyl]benzo[b]thiophen-2-yl]phenoxy]ethyl]pyrrolidine DioxalateAusbeute 439,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140Toluene
Lösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A solution of 1-[2-(4-[3-[4-[3-(1-pyrrolidinyl)-1-propynyl]benzyl]benzo[b]thiophen-2-yl]phenoxy]ethyl]pyrrolidine (Example 129, Part D; 95 mg, 0.182 mmol) in 1.5 mL of toluene was treated with DIBAL-H (455 mL, 0.455 mmol; 1 M in toluene). The resulting mixture was heated at 40° C. for 3 h. The reaction mixture was cooled to 0° C. and quenched with excess MeOH. Saturated K+Na+ tartrate solution and EtOAc (10 mL each) were added, and the biphasic mixture was vigorously stirred for 2 h. The layers were separated, and the aqueous layer was extracted with EtOAc (10 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated. Purification by radial chromatography (SiO2; 98:1.5:0.5 CHCl3—MeOH—NH4OH) afforded 42 mg (0.80 mmol, 44%) of a pale yellow oil which was converted to the dioxalate salt according to the methods detailed in Example 1, Part C.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. customquenched with excess MeOH
  3. additionSaturated K+Na+ tartrate solution and EtOAc (10 mL each) were added
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with EtOAc (10 mL)
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by radial chromatography (SiO2; 98:1.5:0.5 CHCl3—MeOH—NH4OH)

Quellen und Nachweise

ORD-Eintrag
ord-67bc5c31d5344098b8d62d0cf2be5520
Quelldatensatz
uspto-grants-2001_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06251921B1

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