Diisobutylaluminum hydride → (R)-tert-Butyl (1-(4-bromophenyl)-3-oxopropan-2-yl)carbamate

HRID 2384099Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2384099
C[O:2][C:3](=O)[C@H:4]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][CH:7]=1.CC(C[AlH]CC(C)C)C>C(Cl)Cl>[C:17]([O:16][C:14](=[O:15])[NH:13][C@H:4]([CH2:5][C:6]1[CH:7]=[CH:8][C:9]([Br:12])=[CH:10][CH:11]=1)[CH:3]=[O:2])([CH3:20])([CH3:18])[CH3:19]

Komponenten

4

Edukt 2

HCID 14487Diisobutylaluminum hydrideHCID 15735974Boc-4-bromo-D-phenylalanine methyl ester

Produkt 1

HCID 59608321(R)-tert-Butyl (1-(4-bromophenyl)-3-oxopropan-2-yl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Next, to a solution of (R)-3-(4-bromo-phenyl)-2-tert-butoxycarbonylamino-propionic acid methyl ester (1.0 g, 2.79 mmol) in DCM (20 mL) is added DIBAL-H (4.85 mL, 1.0M in DCM) slowly by using syringe pump at −78° C. After the addition is complete the reaction is quenched by adding EtOAc and the mixture is warmed to room temperature. Then a saturated sodium potassium tartaric acid is added and the mixture is and stirred at room temperature for 1 hour. The organic phase is separated and the aqueous layer is extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated to give [(R)-1-(4-bromo-benzyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester which is used directly in the next reaction.

Aufarbeitung

  1. customat −78° C
  2. additionAfter the addition
  3. customis quenched
  4. additionby adding EtOAc
  5. additionThen a saturated sodium potassium tartaric acid is added
  6. customThe organic phase is separated
  7. extractionthe aqueous layer is extracted with EtOAc
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0755e7db328349abb51b52f0bba021f1
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263629B2

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