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

HRID 2406759Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2406759
[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-9d38e2f78e6d41488ab643b4a48555d2
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08809371B2

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