Sodium borohydride → tert-butyl((2S)-3-hydroxyhexan-2-yl)carbamate

HRID 1620111Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1620111
[BH4-].[Na+].[C:3]([O:7][C:8](=[O:17])[NH:9][C@H:10]([C:12](=[O:16])[CH2:13][CH2:14][CH3:15])[CH3:11])([CH3:6])([CH3:5])[CH3:4]>CO.C(O)(C)C>[C:3]([O:7][C:8](=[O:17])[NH:9][C@H:10]([CH:12]([OH:16])[CH2:13][CH2:14][CH3:15])[CH3:11])([CH3:4])([CH3:5])[CH3:6]

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 75406864(S)-tert-butyl(3-oxohexan-2-yl)carbamate

Produkt 1

HCID 87514848tert-butyl((2S)-3-hydroxyhexan-2-yl)carbamateAusbeute 96,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21255859Isopropanol methanolLösungsmittel

Versuchsvorschrift

Sodium borohydride (3.7 g) was added in divided portions to a methanol/isopropanol (30 ml/30 ml) solution containing (S)-tert-butyl(3-oxohexan-2-yl)carbamate (17.5 g) at room temperature, followed by stirring for 1 hour. The solvent was distilled away under reduced pressure, and water was added, followed by extraction with ethyl acetate. The obtained organic layer was washed with saturated saline and dried over anhydrous sodium sulfate, the solvent was distilled away under reduced pressure, and a white solid of tert-butyl((2S)-3-hydroxyhexan-2-yl)carbamate (17 g) was obtained.

Aufarbeitung

  1. distillationThe solvent was distilled away under reduced pressure, and water
  2. additionwas added
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe obtained organic layer was washed with saturated saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled away under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6bb47a9adc174a5ba1b1fb9f95c3bfab
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772320B2

Notizen zur Reaktion

Wird geladen…