Triacetoxyperiodinane → (2S,3S)-tert-Butyl 3-((tert-butyldimethylsilyl)oxy)-2-formylpyrrolidine-1-carboxylate

HRID 751155Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 751155
[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[CH2:21][OH:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[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]

Komponenten

4

Edukt 2

HCID 159087TriacetoxyperiodinaneHCID 109256021,1-Dimethylethyl (2R,3S)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-(hydroxymethyl)-1-pyrrolidinecarboxylate

Produkt 1

HCID 16731848(2S,3S)-tert-Butyl 3-((tert-butyldimethylsilyl)oxy)-2-formylpyrrolidine-1-carboxylateAusbeute 94,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To (2R,3S)-3-(tert-butyl-dimethylsilanyloxy)-2-hydroxymethyl pyrrolidine-1-carboxylic acid tert-butyl ester (61A) (9.85 g, 29.7 mmol) in CH2Cl2 (200 mL) at 0° C. was added Dess-Martin periodinane. The ice bath was removed and the reaction was warmed to rt. After 2 h, saturated aqueous Na2S2O3 and NaHCO3 (ca. 100 mL each) were added and the reaction mixture was stirred vigorously for 0.5 h. The layers were separated, and the organic layer was washed with a mixture of saturated aqueous Na2S2O3 and saturated aqueous NaHCO3 followed by brine, dried (MgSO4), and was then filtered and concentrated to obtain the title compound (9.23 g) as a yellow oil.

Aufarbeitung

  1. customThe ice bath was removed
  2. additionsaturated aqueous Na2S2O3 and NaHCO3 (ca. 100 mL each) were added
  3. customThe layers were separated
  4. washthe organic layer was washed with a mixture of saturated aqueous Na2S2O3 and saturated aqueous NaHCO3
  5. dry with materialdried (MgSO4)
  6. filtrationwas then filtered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-fa8f34ea8de946569936b42350a96f4f
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07405234B2

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