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Phthalimide → (R)-tert-butyl 3-(1,3-dioxoisoindolin-2-yl)-3-(3-fluoro-4-(trifluoromethyl)phenyl)propylcarbamate

HRID 2279534
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2279534
[F:1][C:2]1[CH:3]=[C:4]([C@@H:12](O)[CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].[C:24]1(=[O:34])[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26](=[O:33])[NH:25]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[O:34]=[C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26](=[O:33])[N:25]1[C@@H:12]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([F:11])([F:10])[F:9])=[C:2]([F:1])[CH:3]=1)[CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 86705528(S)-tert-butyl 3-(3-fluoro-4-(trifluoromethyl)phenyl)-3-hydroxypropylcarbamate

Produkt 1

HCID 68294223(R)-tert-butyl 3-(1,3-dioxoisoindolin-2-yl)-3-(3-fluoro-4-(trifluoromethyl)phenyl)propylcarbamateAusbeute 42,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 286 (0.600 g, 1.78 mmol) and THF (15 mL) cooled to 0° C. was added isoindoline-1,3-dione (0.288 g, 1.96 mmol) and PPh3 (0.700 g, 2.67 mmol) followed by the dropwise addition of a THF (6 mL) solution of DEAD (0.420 mL, 2.67 mmol). The reaction was warmed to RT and stirred for 20 h. The reaction was concentrated, triturated with ether and filtered. The resulting filtrate was poured into water and extracted with DCM. The combined organic extracts were dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with hexane/EtOAc (4:1) to afford 0.350 g (42.4%) of (R)-tert-butyl 3-(1,3-dioxoisoindolin-2-yl)-3-(3-fluoro-4-(trifluoromethyl)phenyl)propylcarbamate (288).

Aufarbeitung

  1. concentrationThe reaction was concentrated
  2. customtriturated with ether
  3. filtrationfiltered
  4. additionThe resulting filtrate was poured into water
  5. extractionextracted with DCM
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by SiO2 chromatography
  10. washeluting with hexane/EtOAc (4:1)

Quellen und Nachweise

ORD-Eintrag
ord-6400453aeb9d44c089f94e9dd0a73f93
Quelldatensatz
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09133187B2

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