Triphenylphosphine → 1,1-Dimethylethyl {2-[(4-bromo-3-methylphenyl)oxy]ethyl}carbamate

HRID 70304

Reaktionsgleichung

Reaktionsgleichung von HRID 70304
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].[C:10]([NH:17][CH:18](O)[CH3:19])([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>CCOCC.C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:19][CH2:18][NH:17][C:10](=[O:11])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:4][C:3]=1[CH3:9]

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 728574-Bromo-m-cresolHCID 5363146Diisopropyl azodicarboxylateHCID 22620026t-Butoxycarbonylaminoethanol

Produkt 1

HCID 593164611,1-Dimethylethyl {2-[(4-bromo-3-methylphenyl)oxy]ethyl}carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of 4-bromo-3-methylphenol (0.187 g; 1.00 mmol), N-Boc aminoethanol (0.39 mL; 2.5 mmol) and PPh3 (0.655 g; 2.5 mmol) in anhyd PhH (5 mL) at 0° C. was added DIAD (0.49 mL; 2.5 mmol), dropwise over 15 min. The mixture was stirred 16 h at room temperature, diluted with Et2O, washed (2×satd Na2CO3, 2×H2O, brine), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording the title compound as a colorless gum, which solidified on standing. LC/MS (method A) tR 2.95 min, m/z 330, 332 (M+H, Br isotopes, 2%), 352, 354 (M+Na, Br isotopes, 40-43%), 230, 232 ([M-Boc]+H, Br isotopes, 100%).

Aufarbeitung

  1. washwashed (2×satd Na2CO3, 2×H2O, brine)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-0d9451e55c0b4e4c90d7593d5def4c9b
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822518B2

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