Chlorotrimethylsilane → N-Boc-trans-4-hydroxy-L-prolinol

HRID 604852Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 604852
[Li+].[BH4-].C[Si](Cl)(C)C.[C:8]([O:12][C:13]([N:15]1[CH2:19][C@H:18]([OH:20])[CH2:17][C@H:16]1[C:21](O)=[O:22])=[O:14])([CH3:11])([CH3:10])[CH3:9]>C1COCC1>[OH:20][C@H:18]1[CH2:19][N:15]([C:13]([O:12][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:14])[C@H:16]([CH2:21][OH:22])[CH2:17]1

Komponenten

5

Edukt 3

HCID 6397ChlorotrimethylsilaneHCID 88804(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acidHCID 4148881Lithium borohydride

Produkt 1

HCID 11275979N-Boc-trans-4-hydroxy-L-prolinolAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a 0° C. suspension of LiBH4 (2.0 equiv) in THF (0.67 M) was slowly added TMSCl (4.0 equiv) by syringe. After stirring at room temperature for 30 minutes, (2S,4R)-1-(tert-butoxycarbonyl)-4-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 65% 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-3214679b4de743ad98314c5b4527f59d
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07910743B2

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