Ammonium Chloride → (S)-tert-butyl 1-cyclohexyl-3-hydroxypentan-2-ylcarbamate

HRID 451768

Reaktionsgleichung

Reaktionsgleichung von HRID 451768
[CH:1]1([CH2:7][C@H:8]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[C:9](=[O:12])[CH2:10][CH3:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+].[NH4+].[Cl-]>C1COCC1.CO>[CH:1]1([CH2:7][C@H:8]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH:9]([OH:12])[CH2:10][CH3:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 15730499(S)-tert-butyl 1-cyclohexyl-3-oxopentan-2-ylcarbamate

Produkt 1

HCID 59201568(S)-tert-butyl 1-cyclohexyl-3-hydroxypentan-2-ylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (S)-tert-butyl 1-cyclohexyl-3-oxopentan-2-ylcarbamate in THF/MeOH (604/15 mL) at 0° C. was carefully added NaBH4 (630 mg, 16.66 mmol). After 20 min, sat. aq. NH4Cl was added to quench the reaction, and extracted with EtOAc, washed with brine, dried over Na2SO4, filtered, and concentrated to give (S)-tert-butyl 1-cyclohexyl-3-hydroxypentan-2-ylcarbamate (4.77 g, 96%, in a ratio of 40:60) as a white solid. MS ESI +ve m/z 286 (M+H).

Aufarbeitung

  1. customat 0° C.
  2. customto quench
  3. customthe reaction
  4. extractionextracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0db4cce6a1e04c7090574e707c3d1e2a
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08487108B2

Verknüpfte Notizen

Wird geladen…