Phthalimide → (R)-2-(2-methyl-4,4,4-trifluorobutyl)-1H-isoindole-1,3(2H)-dione

HRID 327810Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 327810
N(C(OCC)=O)=NC(OCC)=O.[CH3:13][C@H:14]([CH2:17][C:18]([F:21])([F:20])[F:19])[CH2:15]O.[C:22]1(=[O:32])[NH:26][C:25](=[O:27])[C:24]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:23]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(OCC)C.O1CCCC1>[CH3:13][C@H:14]([CH2:17][C:18]([F:21])([F:20])[F:19])[CH2:15][N:26]1[C:22](=[O:32])[C:23]2[C:24](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:25]1=[O:27]

Komponenten

7

Edukt 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 10351792(2R)-4,4,4-trifluoro-2-methylbutan-1-ol

Produkt 1

HCID 10378474(R)-2-(2-methyl-4,4,4-trifluorobutyl)-1H-isoindole-1,3(2H)-dioneAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Diethyl azodicarboxylate (15.4 mL) was added to a 0° C., stirred slurry of (R)-2-methyl-4,4,4-trifluorobutan-1-ol (about 12.0 g), phthalimide (13.4 g), and triphenylphosphine (23.7 g) in diethyl ether (about 6.5 g, see above) and dry tetrahydrofuran (110 mL), warmed to room temperature overnight, and stirred an additional 8 h. The mixture was evaporated, methylene chloride was added to the residue, and the slurry was filtered. The filtrate was purified by flash chromatography, eluting with 1:1 methylene chloride:hexanes, to give (R)-2-(2-methyl-4,4,4-trifluorobutyl)-1H-isoindol-1,3(2H)-dione (17.1 g, 75%) as a white solid; mp 45°-47° C.; partial NMR (400 MHz, CDCl3): 1.08(d,3H,CH3), 1.94-2.07 (m,1H,CF3CH2), 2.14-2.31(m,1H,CF3CH2), 2.36-2.50(m,1H,CHCH3), 3.58(dd,1H,CH2N), 3.64(dd,1H,CH2N).

Aufarbeitung

  1. customThe mixture was evaporated
  2. additionmethylene chloride was added to the residue
  3. filtrationthe slurry was filtered
  4. customThe filtrate was purified by flash chromatography
  5. washeluting with 1:1 methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-5bda010e5c5d49ca91357c9d837abefe
Quelldatensatz
uspto-grants-1993_12
Patentnummer
US05274118

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