(2S-trans)-4-cyclohexyl-5-oxo-2-pyrrolidinemethanol → (2S-trans)-4-cyclohexyl-2-pyrrolidinemethanol

HRID 280385Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 280385
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1([C@H:13]2[C:17](=O)[NH:16][C@H:15]([CH2:19][OH:20])[CH2:14]2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1>O1CCCC1>[CH:7]1([C@H:13]2[CH2:17][NH:16][C@H:15]([CH2:19][OH:20])[CH2:14]2)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1

Komponenten

4

Edukt 2

HCID 13648265(2S-trans)-4-cyclohexyl-5-oxo-2-pyrrolidinemethanolHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 13648259(2S-trans)-4-cyclohexyl-2-pyrrolidinemethanolAusbeute 37,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of lithium aluminum hydride (0.8 g) in 50 ml of tetrahydrofuran was added (2S-trans)-4-cyclohexyl-5-oxo-2-pyrrolidinemethanol (2.0 g) in 20 ml of tetrahydrofuran. After the addition, the mixture was refluxed for 24 hours, cooled to 0° C., quenched with ethyl acetate followed by saturated sodium sulphate solution, filtered, and the filtrate dried over anhydrous magnesium sulphate. Removal of the solvent followed by crystallization yielded 0.7 g of (2S-trans)-4-cyclohexyl-2-pyrrolidinemethanol as white crystals, melting point 98°-99° C.

Aufarbeitung

  1. additionAfter the addition
  2. temperaturethe mixture was refluxed for 24 hours
  3. customquenched with ethyl acetate
  4. filtrationfiltered
  5. dry with materialthe filtrate dried over anhydrous magnesium sulphate
  6. customRemoval of the solvent
  7. customfollowed by crystallization

Quellen und Nachweise

ORD-Eintrag
ord-8dd6d9d30e1b4339abf0d414f43e8a58
Quelldatensatz
uspto-grants-1986_05
Patentnummer
US04588819

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