(Triphenylphosphoranylidene)acetonitrile → ((R)-3-cyano-1-methyl-allyl)-carbamic acid tert-butyl ester

HRID 246215

Reaktionsgleichung

Reaktionsgleichung von HRID 246215
[C:1]([O:5][C:6](=[O:12])[NH:7][C@H:8]([CH3:11])[CH:9]=O)([CH3:4])([CH3:3])[CH3:2].C1(P(=[CH:32][C:33]#[N:34])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[C:1]([O:5][C:6](=[O:12])[NH:7][C@H:8]([CH3:11])[CH:9]=[CH:32][C:33]#[N:34])([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 85524(Triphenylphosphoranylidene)acetonitrileHCID 10910049tert-butyl N-((2R)-1-oxopropan-2-yl)carbamate

Produkt 1

HCID 86677956((R)-3-cyano-1-methyl-allyl)-carbamic acid tert-butyl esterAusbeute 63,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In a 20 mL scintillation vial, ((R)-1-methyl-2-oxo-ethyl)-carbamic acid tert-butyl ester (2.5 g, 14.4 mmol) and (triphenylphosphoranylidene)acetonitrile (6.52 g, 21.7 mmol) were mixed in dichloromethane (20 mL) and stirred at room temperature for 16 h. The solvent was evaporated to give the crude material, which was purified by column chromatography (silica gel, gradient n-hexanes ethyl acetate) to provide 1.8 g (63%) of ((R)-3-cyano-1-methyl-allyl)-carbamic acid tert-butyl ester in a 3:1 diastereoselectivity (E:Z) as a colorless oil. 1H NMR (300 MHz, CDCl3) δ ppm 6.38-6.79 (m, 1H), 5.47 (dd, J=16.24, 1.89 Hz, 1H), 4.48 (bs, 1H), 4.47 (bs, 1H), 1.45 (s, 1H), 1.28 (d, J=7.18 Hz, 9H).

Aufarbeitung

  1. customThe solvent was evaporated
  2. customto give the crude material, which
  3. customwas purified by column chromatography (silica gel, gradient n-hexanes ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-fc346cea310b4a4e9983a907bd66bedf
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658646B2

Verknüpfte Notizen

Wird geladen…