tert-Butyl-(2S,3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-formylpyrrolidine-1-carboxylate → (2R,3R)-3-(tert-Butyl-dimethylsilanyloxy)-2-[(1S)-(1-hydroxy-2-methylpropyl)]pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 751143Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 751143
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[C@H:9]1[CH:21]=[O:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:23]([Mg]Cl)([CH3:25])[CH3:24]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[C@H:9]1[C@@H:21]([OH:22])[CH:23]([CH3:25])[CH3:24])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 16732142tert-Butyl-(2S,3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-formylpyrrolidine-1-carboxylateHCID 178418918HCID 178418918, Verbindung

Produkt 1

HCID 68459442(2R,3R)-3-(tert-Butyl-dimethylsilanyloxy)-2-[(1S)-(1-hydroxy-2-methylpropyl)]pyrrolidine-1-carboxylic acid tert-butyl esterAusbeute 79,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-60 °C

Versuchsvorschrift

To 51C (6.50 g, 19.8 mmol) in THF (100 mL) at −78° C. was added a 2M THF solution of isopropylmagnesium chloride (30.0 mL, 60.0 mmol) over 20 min. The cold bath was removed and the reaction was stirred for 1 h. The reaction was then cooled to −60° C. and was quenched with saturated aqueous ammonium chloride. After warming to rt, the whole was diluted with EtOAc. The layers were separated and the organic layer washed with water and brine, then dried (MgSO4), filtered and concentrated. The resulting residue was purified via flash chromatography eluting with 20% EtOAc/hexane to provide the title compound (5.90 g).

Aufarbeitung

  1. customThe cold bath was removed
  2. customwas quenched with saturated aqueous ammonium chloride
  3. temperatureAfter warming to rt
  4. additionthe whole was diluted with EtOAc
  5. customThe layers were separated
  6. washthe organic layer washed with water and brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe resulting residue was purified via flash chromatography
  11. washeluting with 20% EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-69203770de73429e89a5770bc9604a89
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07405234B2

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