Aluminium lithium hydride → (1-Benzyl-3-methoxymethylpyrrolidin-3-yl)methanol

HRID 10357

Reaktionsgleichung

Reaktionsgleichung von HRID 10357
[CH2:1]([O:3][C:4]([C:6]1([CH2:18][O:19]C)[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7]1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:11]([N:8]1[CH2:9][CH2:10][C:6]([CH2:18][OH:19])([CH2:4][O:3][CH3:1])[CH2:7]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 690697751-Benzyl-3-methoxymethylpyrrolidine-3-carboxylic acid ethyl ester

Produkt 1

HCID 21979083(1-Benzyl-3-methoxymethylpyrrolidin-3-yl)methanolAusbeute 87,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 1-benzyl-3-methoxymethylpyrrolidine-3-carboxylic acid ethyl ester (Example A18a, 2.30 g, 8.3 mmol) in anhydrous tetrahydrofuran (10 mL) is added dropwise to an ice-cold suspension of lithium aluminum hydride (0.821 g, 22 mmol) in tetrahydrofuran (50 mL). The resulting mixture is stirred at room temperature for 18 hours, cooled and quenched by the sequential dropwise addition of 1N sodium hydroxide and water. The solids are removed by filtration, re-suspended in hot tetrahydrofuran and filtered. The combined filtrates are concentrated in vacuo and the residue is partitioned between dichloromethane and water. The organic extracts are dried over Na2SO4, filtered and concentrated under vacuum to afford the title compound (1.71 g). 1N NMR (200 MHz, CDCl3): δ 7.41–7.17 (m, 5H), 3.84–3.43 (m, 4H), 3.34 (s, 2H), 3.32 (s, 3H), 2.85–2.60 (m, 2H), 2.54–2.14 (m, 3H), 1.98–1.50 (m, 2H).

Aufarbeitung

  1. temperaturecooled
  2. customquenched by the sequential dropwise addition of 1N sodium hydroxide and water
  3. customThe solids are removed by filtration
  4. filtrationfiltered
  5. concentrationThe combined filtrates are concentrated in vacuo
  6. customthe residue is partitioned between dichloromethane and water
  7. dry with materialThe organic extracts are dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-e346e5323871419b8510bb1982209d01
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094780B1

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