[4-(4-Cyanophenyl)but-3-ynyl]carbamic acid tert-butyl ester → [4-(4-Cyanophenyl)butyl]carbamic acid tert-butyl ester

HRID 81340

Reaktionsgleichung

Reaktionsgleichung von HRID 81340
[C:1]([O:5][C:6](=[O:20])[NH:7][CH2:8][CH2:9][C:10]#[C:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].C(O)C>[C:1]([O:5][C:6](=[O:20])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]#[N:19])=[CH:16][CH:17]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 2

HCID 67364707[4-(4-Cyanophenyl)but-3-ynyl]carbamic acid tert-butyl esterHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 67366079[4-(4-Cyanophenyl)butyl]carbamic acid tert-butyl esterAusbeute 87,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A suspension of [4-(4-cyanophenyl)but-3-ynyl]carbamic acid tert-butyl ester 56 (5.2 g, 19.2 mmol) and 10% palladium on carbon (2.5 g, wet) in ethanol/THE (30 mL, 1:1) was stirred overnight under 1 atmosphere of hydrogen. After purging with nitrogen, the reaction mixture was suction filtered through a pad of Celite. The solvent was removed from the filtrate by evaporation. The residue was chromatographed on silica gel, eluting with methylene chloride/ethyl acetate (30:1), to afford the pure product 57 (4.6 g, 87%) as an oil. 1H NMR (300 MHz, CDCl3) δ 1.44 (s, 9H), 1.51 (m, 2H), 1.65 (m, 2H), 2.69 (t, 2H), 3.14 (m, 2H), 4.52 (br s, 1H), 7.27 (d, 2H), 7.56 (d, 2H).

Aufarbeitung

  1. customAfter purging with nitrogen
  2. filtrationfiltered through a pad of Celite
  3. customThe solvent was removed from the filtrate by evaporation
  4. customThe residue was chromatographed on silica gel
  5. washeluting with methylene chloride/ethyl acetate (30:1)

Quellen und Nachweise

ORD-Eintrag
ord-8dac3a66badc4fa2b709fec25abc6ec0
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846688B2

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