HCID 10854740, Verbindung → tert-butyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-(propan-2-yl)pyrrolidine-1-carboxylate

HRID 1852734Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1852734
[Si:1]([O:8][C@H:9]1[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@H:11]([C:21]([CH3:23])=[CH2:22])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>CO.[Ni]>[Si:1]([O:8][C@H:9]1[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@H:11]([CH:21]([CH3:23])[CH3:22])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Komponenten

4

Edukt 1

HCID 10854740HCID 10854740, Verbindung

Produkt 1

HCID 86724490tert-butyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-(propan-2-yl)pyrrolidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of tert-butyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-(prop-1-en-2-yl)pyrrolidine-1-carboxylate (90 g) dissolved in methanol (250 mL) was added Raney Nickel (24 g). The reaction mixture was stirred under hydrogen (40 atm) at 60° C. for 3 hours. The mixture was filtered and concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with brine (2×50 mL), dried over magnesium sulfate, filtered and concentrated to give tert-butyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-(propan-2-yl)pyrrolidine-1-carboxylate. The residue was used directly without further purification.

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with brine (2×50 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5df3d102afee42daaea2081d92930503
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962611B2

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