Chlorotrimethylsilane → tert-butyl (2R,3S)-3-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate

HRID 495056Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 495056
[Li+].[BH4-].C[Si](Cl)(C)C.[C:8]([O:12][C:13]([N:15]1[CH2:19][CH2:18][C@H:17]([OH:20])[C@H:16]1[C:21](O)=[O:22])=[O:14])([CH3:11])([CH3:10])[CH3:9]>C1COCC1>[OH:20][C@H:17]1[CH2:18][CH2:19][N:15]([C:13]([O:12][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:14])[C@@H:16]1[CH2:21][OH:22]

Komponenten

5

Edukt 3

HCID 6397ChlorotrimethylsilaneHCID 4148881Lithium borohydrideHCID 14037017(2S,3S)-1-(tert-Butoxycarbonyl)-3-hydroxypyrrolidine-2-carboxylic acid

Produkt 1

HCID 10910976tert-butyl (2R,3S)-3-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylateAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a 0° C. suspension of LiBH4 (2.0 equiv) in THF (0.5 M) was slowly added TMSCl (4.0 equiv) by syringe. After stirring at room temperature for 30 minutes, (2S,3S)-1-(tert-butoxycarbonyl)-3-hydroxypyrrolidine-2-carboxylic acid (1.0 equiv) was then added, and the resulting mixture was stirred at room temperature overnight. The reaction was quenched by the careful addition of sat'd. aq. NaHCO3, and the mixture was diluted with EtOAc, and the organice layer was washed twice with sat'd. aq. NaHCO3, once with brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The title compound was isolated in 55% yield and used without further purification.

Aufarbeitung

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. customThe reaction was quenched by the careful addition of sat'd
  3. additionaq. NaHCO3, and the mixture was diluted with EtOAc
  4. washthe organice layer was washed twice with sat'd
  5. dry with materialaq. NaHCO3, once with brine, dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d2cfc07b7a56484f81ae914204a2b9c8
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538223B2

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