Aluminium lithium hydride → HCID 59497801, Verbindung

HRID 1011511Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1011511
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([NH:17][C@H:18]2[CH2:22][CH2:21][CH2:20][C@H:19]2[C:23](OCC)=[O:24])(=[O:16])=[O:15])=[CH:10][CH:9]=1>O1CCCC1>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([NH:17][C@@H:18]2[CH2:22][CH2:21][CH2:20][C@@H:19]2[CH2:23][OH:24])(=[O:15])=[O:16])=[CH:10][CH:9]=1

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 90811846cis-Ethyl 2-(4-chlorophenylsulfonamido)cyclopentanecarboxylate

Produkt 1

HCID 59497801HCID 59497801, VerbindungAusbeute 100,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A 1.0 M solution of lithium aluminum hydride in tetrahydrofuran (9.36 mL, 9.36 mmol) was added dropwise to a solution of cis-ethyl 2-(4-chlorophenylsulfonamido)cyclopentanecarboxylate (2.07 g, 6.24 mmol) in 40 mL anhydrous tetrahydrofuran under nitrogen at 0° C. The reaction was then stirred for 1 h at room temperature, then quenched by the slow addition of 100 mL ethyl acetate. The reaction was partitioned between 600 mL ethyl acetate and 300 mL saturated ammonium chloride. The organic layer was dried on sodium sulfate and concentrated to yield 4-chloro-N-(cis-2-(hydroxymethyl)cyclopentyl)benzenesulfonamide (1.81 g, 100%). 1H NMR (400 MHz, CDCl3) δ ppm 7.77-7.85 (2H, m), 7.45-7.50 (2H, m), 5.38 (1H, d, J=7.05 Hz), 3.61-3.78 (3H, m), 2.04-2.15 (1H, m), 1.27-1.80 (7H, m). LC/MS R.T.=2.46 min; [M+H]+=290.10.

Aufarbeitung

  1. customquenched by the slow addition of 100 mL ethyl acetate
  2. customThe reaction was partitioned between 600 mL ethyl acetate and 300 mL saturated ammonium chloride
  3. customThe organic layer was dried on sodium sulfate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-4840887b7fa34988ad7c16830b6ae509
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977362B2

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