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Toluene → HCID 117925141, Verbindung

HRID 705715
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 705715
[C:1]([O:5][C:6]([N:8]1[C@H:14]([CH2:15]O)[CH2:13][CH2:12][C@@H:11]2[C@H:9]1[CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:17]1(=[O:27])[NH:21][C:20](=[O:22])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.C1(C)C=CC=CC=1>C1COCC1.O>[C:1]([O:5][C:6]([N:8]1[C@H:14]([CH2:15][N:21]2[C:17](=[O:27])[C:18]3[C:19](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:20]2=[O:22])[CH2:13][CH2:12][C@@H:11]2[C@H:9]1[CH2:10]2)=[O:7])([CH3:2])([CH3:3])[CH3:4]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 1140TolueneHCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 89872603tert-Butyl (1R,3S,6S)-3-(hydroxymethyl)-2-azabicyclo[4.1.0]heptane-2-carboxylate

Produkt 1

HCID 117925141HCID 117925141, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A suspension of D7 (10 g, 44 mmol), phtalimide (10.29 g, 70 mmol) and triphenylphosphine (18.34 g, 70 mmol) in THF (150 mL) was cooled at 0° C., then a 40% solution of DEAD in toluene (31.94 mL, 70 mmol) was added. The mixture was stirred at room temperature for 3 hours, then water was added and the mixture was concentrated under vacuum; the residue was dissolved in DCM, washed with water and organics were evaporated. Cyclohexane (300 mL) and DCM (10 mL) were added, the precipitate was discarded and the filtrate was concentrated. The crude mixture was purified by silica gel column chromatography (cyclohexane/ethyl acetate=95:5 to 70/30) to give the title compound as a white solid. Yield (11 g, 71%).

Aufarbeitung

  1. concentrationthe mixture was concentrated under vacuum
  2. dissolutionthe residue was dissolved in DCM
  3. washwashed with water
  4. customorganics were evaporated
  5. additionCyclohexane (300 mL) and DCM (10 mL) were added
  6. concentrationthe filtrate was concentrated
  7. customThe crude mixture was purified by silica gel column chromatography (cyclohexane/ethyl acetate=95:5 to 70/30)

Quellen und Nachweise

ORD-Eintrag
ord-27cb8e22c66545bcac440d3da6d74273
Quelldatensatz
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09174977B2

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