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Ammonium Chloride → tert-butyl (8aS)-7-(3-fluorobenzyl)-6-oxohexahydropyrrolo[1,2-a]pyrazine-2(1H)-carboxylate

HRID 240458
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 240458
[O:1]=[C:2]1[N:6]2[CH2:7][CH2:8][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:10][CH:5]2[CH2:4][CH2:3]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Br[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[CH:31]=1.[NH4+].[Cl-]>O1CCCC1>[F:36][C:32]1[CH:31]=[C:30]([CH:35]=[CH:34][CH:33]=1)[CH2:29][CH:3]1[C:2](=[O:1])[N:6]2[CH2:7][CH2:8][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:10][C@@H:5]2[CH2:4]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 680073-Fluorobenzyl bromideHCID 2733832Lithium hexamethyldisilazaneHCID 82863310tert-butyl 6-oxohexahydropyrrolo[1,2-a]pyrazine-2(1H)-carboxylate

Produkt 1

HCID 86680467tert-butyl (8aS)-7-(3-fluorobenzyl)-6-oxohexahydropyrrolo[1,2-a]pyrazine-2(1H)-carboxylateAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-40 °C

Versuchsvorschrift

To a solution of the product from Example 207A (0.10 g, 0.416 mmol) in anhydrous tetrahydrofuran (4 mL) at −78° C. under N2 was added a 1 M solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (0.458 mL, 0.458 mmol) dropwise over 2 minutes. To the resulting solution was added 1-(bromomethyl)-3-fluorobenzene (0.056 mL, 0.458 mmol), and the resulting mixture was stirred at −40° C. for 3 hours. A solution of NH4Cl (10% in water, 1 mL) was added, and the mixture was allowed to warm to room temperature and partitioned between water and ethyl acetate (3×). The combined organic layers were dried over Na2SO4. The drying agent was removed by filtration, and the filtrate was concentrated in vacuo. The crude product was purified by column chromatography on silica gel using a solvent gradient of 0-10% CH3OH in CH2Cl2 to give the title compound (75 mg, 52%).

Aufarbeitung

  1. temperatureto warm to room temperature
  2. custompartitioned between water and ethyl acetate (3×)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. customThe drying agent was removed by filtration
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe crude product was purified by column chromatography on silica gel using a solvent gradient of 0-10% CH3OH in CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-8cddb0b7e6d341ca8405a75ed815e58c
Quelldatensatz
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08648074B2

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