tert-Butyl 2-(2-methoxy-2-oxoethyl)pyrrolidine-1-carboxylate → tert-Butyl 2-(2-hydroxyethyl)pyrrolidine-1-carboxylate

HRID 538675Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 538675
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([O:11][C:12]([N:14]1[CH2:18][CH2:17][CH2:16][CH:15]1[CH2:19][C:20](OC)=[O:21])=[O:13])([CH3:10])([CH3:9])[CH3:8]>C1COCC1>[C:7]([O:11][C:12]([N:14]1[CH2:18][CH2:17][CH2:16][CH:15]1[CH2:19][CH2:20][OH:21])=[O:13])([CH3:10])([CH3:9])[CH3:8]

Komponenten

4

Edukt 2

HCID 13425758tert-Butyl 2-(2-methoxy-2-oxoethyl)pyrrolidine-1-carboxylateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 13425759tert-Butyl 2-(2-hydroxyethyl)pyrrolidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a stirred solution of LAH (0.94 g, 24.69 mmol) in dry THF (100 mL) was added solution of compound 36 (3.0 g 12.34 mmol) in THF (40 mL) at 0° C. and stirred at rt for 16 hours. The reaction mixture was quenched with brine solution and filtered through a Celite® bed. The organic layer was dried over anhydrous Na2SO4 and evaporated. The crude was purified by Combiflash® chromatography eluting with 2-3% of methanol-DCM to provide liquid compound 37.

Aufarbeitung

  1. customThe reaction mixture was quenched with brine solution
  2. filtrationfiltered through a Celite® bed
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. customevaporated
  5. customThe crude was purified by Combiflash® chromatography
  6. washeluting with 2-3% of methanol-DCM

Quellen und Nachweise

ORD-Eintrag
ord-74fd2e7bcf1e43e4a15dd9826b81b4a9
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865741B2

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