Bromide ion → methyl (S)-3,3-dimethylbutan-2-yl(3-(4-fluorophenyl)-3-hydroxyhex-5-enyl)carbamate

HRID 2091512Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2091512
[CH3:1][C:2]([CH3:22])([CH3:21])[C@@H:3]([N:5]([CH2:10][CH2:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)=[O:13])[C:6](=[O:9])[O:7][CH3:8])[CH3:4].[Br-].[CH2:24]1[CH2:28]OC[CH2:25]1>>[CH3:22][C:2]([CH3:21])([CH3:1])[C@@H:3]([N:5]([CH2:10][CH2:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)([OH:13])[CH2:28][CH:24]=[CH2:25])[C:6](=[O:9])[O:7][CH3:8])[CH3:4]

Komponenten

4

Edukt 3

HCID 259Bromide ionHCID 8028TetrahydrofuranHCID 58485254(S)-methyl 3,3-dimethylbutan-2-yl(3-(4-fluorophenyl)-3-oxopropyl)carbamate

Produkt 1

HCID 58485267methyl (S)-3,3-dimethylbutan-2-yl(3-(4-fluorophenyl)-3-hydroxyhex-5-enyl)carbamateAusbeute 92 %

Versuchsvorschrift

To a solution of (S)-methyl 3,3-dimethylbutan-2-yl(3-(4-fluorophenyl)-3-oxopropyl)carbamate (4.5 g, 0.015 mol) in THF (60 mL) was added allymagnesium bromide (1 M, 30 mL, 0.03 mol) dropwise at −78° C. under N2. After adding completely, the reaction mixture was stirred at rt overnight. The reaction was quenched with saturated aqueous NH4Cl solution, and the mixture was extracted with EtOAc. The combined organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to give methyl (S)-3,3-dimethylbutan-2-yl(3-(4-fluorophenyl)-3-hydroxyhex-5-enyl)carbamate (4.80 g, 92%), which was used for the next step without further purification.

Aufarbeitung

  1. additionAfter adding completely
  2. customThe reaction was quenched with saturated aqueous NH4Cl solution
  3. extractionthe mixture was extracted with EtOAc
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a3bd46523c3247459ff69ddd72a83521
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08440658B2

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