Lithium borohydride → [6-(3-Hydroxy-4-hydroxymethyl-pyrrolidin-1-yl)-6-oxo-hexyl]-carbamic Acid Benzyl Ester

HRID 2403012

Reaktionsgleichung

Reaktionsgleichung von HRID 2403012
[BH4-].[Li+].C([O:5][C:6]([CH:8]1[CH:12]([OH:13])[CH2:11][N:10]([C:14](=[O:31])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[CH2:9]1)=O)C>O1CCCC1.CO.C(Cl)(Cl)Cl>[CH2:24]([O:23][C:21](=[O:22])[NH:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][C:14]([N:10]1[CH2:9][CH:8]([CH2:6][OH:5])[CH:12]([OH:13])[CH2:11]1)=[O:31])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Komponenten

5

Edukt 2

HCID 4148881Lithium borohydrideHCID 686374701-(6-Benzyloxycarbonylamino-hexanoyl)-4-hydroxy-pyrrolidine-3-carboxylic Acid Ethyl Ester

Produkt 1

HCID 68637867[6-(3-Hydroxy-4-hydroxymethyl-pyrrolidin-1-yl)-6-oxo-hexyl]-carbamic Acid Benzyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 21584188Chloroform methanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To the solution of lithium borohydride (0.305 g, 13 mmol) in anhydrous tetrahydrofuran (25 mL) was added a solution of ethyl ester 62 (3.74 g, 9.2 mmol) in THF (25 mL) over a period of 30 mins at 0° C. After the addition the reaction mixture was brought to room temperature and stirred further under argon. The completion of the reaction was ascertained by TLC after 4 h. (Rf=0.4 in 10% MeOH/CHCl3). The reaction mixture was evaporated to dryness and cooled to 0° C. To the residue 3N HCl (40 mL) was added slowly. After stirring for 30 mins the product was extracted with dichloromethane (3×75 mL). The combined organic layer was washed with brine and dried over sodium sulfate. Organic layer was filtered and evaporated to dryness. Compound 63 was purified by column chromatography first by eluting with dichloromethane/methanol (5%) (3.2 g, 92%).

Aufarbeitung

  1. additionAfter the addition the reaction mixture
  2. customwas brought to room temperature
  3. customThe reaction mixture was evaporated to dryness
  4. additionTo the residue 3N HCl (40 mL) was added slowly
  5. stirringAfter stirring for 30 mins the product
  6. extractionwas extracted with dichloromethane (3×75 mL)
  7. washThe combined organic layer was washed with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationOrganic layer was filtered
  10. customevaporated to dryness
  11. customCompound 63 was purified by column chromatography first
  12. washby eluting with dichloromethane/methanol (5%) (3.2 g, 92%)

Quellen und Nachweise

ORD-Eintrag
ord-ea074f23f2e040f39d470fcd600f5bb5
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08796436B2

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