Diethyl Ether → HCID 59281702, Verbindung

HRID 1408939

Reaktionsgleichung

Reaktionsgleichung von HRID 1408939
[CH3:1]COCC.C[Li].[O:8]=[C:9]1[CH2:13][CH2:12][CH2:11][CH:10]1[NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18].[Cl-].[Ce+3].[Cl-].[Cl-]>O1CCCC1>[OH:8][C:9]1([CH3:1])[CH2:13][CH2:12][CH2:11][CH:10]1[NH:14][C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:20])[CH3:19]

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 24636Cerium(III) chlorideHCID 357962tert-butyl N-(2-oxocyclopentyl)carbamateHCID 178418348HCID 178418348, Verbindung

Produkt 1

HCID 59281702HCID 59281702, VerbindungAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A 1.6 M ether solution of methyllithium (13.59 mL, 21.75 mmol) was added to a stirred suspension of tert-butyl 2-oxocyclopentylcarbamate (1.97 g, 9.89 mmol, from Step 2) and cerium(III) chloride (5.36 g, 21.75 mmol) in tetrahydrofuran (50 mL) at −78° C. under nitrogen. After 2.5 h at −78° C., the mixture was quenched with saturated ammonium chloride, allowed to warm to room temperature, and filtered through a short bed of Celite to remove insoluble cerium salt. The filter cake was rinsed with ethyl acetate. The filtrated was extracted with ethyl acetate three times. The combined ethyl acetate phase was washed with saturated ammonium chloride and brine respectively, dried (MgSO4), filtered and concentrated. Silica gel chromatography, eluting with 0 to 50% ethyl acetate in hexanes, gave tert-butyl 2-hydroxy-2-methylcyclopentylcarbamate as yellow solid (1.47 g, 82% yield). 1H NMR analysis indicated the presence of approximately a 3:1 diastereomeric mixture.

Aufarbeitung

  1. customthe mixture was quenched with saturated ammonium chloride
  2. filtrationfiltered through a short bed of Celite
  3. customto remove insoluble cerium salt
  4. washThe filter cake was rinsed with ethyl acetate
  5. extractionThe filtrated was extracted with ethyl acetate three times
  6. washThe combined ethyl acetate phase was washed with saturated ammonium chloride and brine respectively
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. washSilica gel chromatography, eluting with 0 to 50% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-8036fafc7a4e4e8e842ad322318190fa
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921368B2

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