(R,E)-ethyl 5-(tert-butoxycarbonylamino)hex-2-enoate → (R)-ethyl 5-(tert-butoxycarbonylamino)hexanoate

HRID 529549Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 529549
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH3:18])[CH2:10]/[CH:11]=[CH:12]/[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)C.[Pd]>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH3:18])[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 86706226(R,E)-ethyl 5-(tert-butoxycarbonylamino)hex-2-enoateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 86706227(R)-ethyl 5-(tert-butoxycarbonylamino)hexanoateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A suspension of (R,E)-ethyl 5-(tert-butoxycarbonylamino)hex-2-enoate (1.70 g, 6.61 mmol) and 5% Pd/C (350 mg) in ethanol (35 mL) was vigorously stirred under the atmosphere of hydrogen balloon for 1.5 hr. The reaction mixture was filtered and the filtrate were concentrated to give (R)-ethyl 5-(tert-butoxycarbonylamino)hexanoate (1.71 g, 6.58 mmol, 100% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ ppm 4.34 (s, 1H), 4.12 (q, J=7.1 Hz, 2H), 3.66 (s, 1H), 2.31 (td, J=7.5, 1.6 Hz, 2H), 1.75-1.57 (m, 2H), 1.51-1.38 (m, 2H), 1.44 (s, 9H), 1.25 (t, J=7.1 Hz, 3H), 1.12 (d, J=6.6 Hz, 3H).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate were concentrated

Quellen und Nachweise

ORD-Eintrag
ord-9f7832225c3a45bbb1469db306250068
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346852B2

Notizen zur Reaktion

Wird geladen…