Sodium borohydride → tert-Butyl ((2S,4R)-1-hydroxy-4-(hydroxymethyl)hept-6-en-2-yl)carbamate

HRID 451969Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 451969
[CH2:1]([C@H:4]1[C:8](=[O:9])[N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:6]([C:17](OCC)=[O:18])[CH2:5]1)[CH:2]=[CH2:3].[BH4-].[Na+]>CO.O>[OH:18][CH2:17][C@@H:6]([NH:7][C:10](=[O:11])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:5][C@H:4]([CH2:8][OH:9])[CH2:1][CH:2]=[CH2:3]

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 5287387(2S,4R)-1-tert-butyl 2-ethyl 4-allyl-5-oxopyrrolidine-1,2-dicarboxylate

Produkt 1

HCID 58011569tert-Butyl ((2S,4R)-1-hydroxy-4-(hydroxymethyl)hept-6-en-2-yl)carbamateAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22242641Methanol--water (1/1)Lösungsmittel

Versuchsvorschrift

To a solution of (2S,4R)-1-tert-butyl 2-ethyl 4-allyl-5-oxopyrrolidine-1,2-dicarboxylate (30 g, 0.1 mol) in MeOH/H2O (700/70 mL) was added NaBH4 (25 g, 0.66 mol), the result mixture was stirred 1 hr at rt and quenched with sat. aq. NH4Cl (300 mL). The organic solvent was removed under vacuum and extracted with EtOAc (3×250 mL). The combined organic phases were washed with brine (250 mL) and dried over anhydrous Na2SO4, filtered and evaporated to afford crude tert-butyl (2S,4R)-1-hydroxy-4-(hydroxymethyl)hept-6-en-2-ylcarbamate (22 g, 85%). It was used in the next step without further purification.

Aufarbeitung

  1. customquenched with sat. aq. NH4Cl (300 mL)
  2. customThe organic solvent was removed under vacuum
  3. extractionextracted with EtOAc (3×250 mL)
  4. washThe combined organic phases were washed with brine (250 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-28b8fc0877fc418d991aea9b4ddfe46c
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08487108B2

Notizen zur Reaktion

Wird geladen…