N-Hydroxyphthalimide → 2-{[1-(Diphenylmethyl)azetidin-3-yl]oxy}-1H-isoindole-1,3(2H)-dione

HRID 2172012

Reaktionsgleichung

Reaktionsgleichung von HRID 2172012
[CH:1]([N:14]1[CH2:17][CH:16]([OH:18])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[N:20]1[C:24](=[O:25])[C:23]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]2[C:21]1=[O:30].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:2]1([CH:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:14]2[CH2:17][CH:16]([O:18][N:20]3[C:24](=[O:25])[C:23]4[C:22](=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:21]3=[O:30])[CH2:15]2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 3304481-(Diphenylmethyl)azetidin-3-olHCID 5462977Diethyl azodicarboxylate

Produkt 1

HCID 683380242-{[1-(Diphenylmethyl)azetidin-3-yl]oxy}-1H-isoindole-1,3(2H)-dioneAusbeute 37,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of N-benzhydrylazetidin-3-ol (1.0 g, 4.18 mmol) in anhydrous THF (66 mL) under nitrogen were added N-hydroxyphthalimide (750 mg, 4.60 mmol) and triphenylphosphine (2.19 g, 8.36 mmol). The reaction mixture was cooled to 0° C. and DEAD (1.52 mL, 8.36 mmol) was added dropwise. The solution was allowed to warm to room temperature and stirred overnight. The reaction mixture was concentrated under reduced. The residue was purified on column chromatography (eluent: pentane/EtOAc 7/3 to 4/6) to give the title compound (600 mg, 37%) as a wax.

Aufarbeitung

  1. temperatureto warm to room temperature
  2. concentrationThe reaction mixture was concentrated
  3. customThe residue was purified on column chromatography (eluent: pentane/EtOAc 7/3 to 4/6)

Quellen und Nachweise

ORD-Eintrag
ord-d0a31ed623b44b9582b5a1c6d06ff3fe
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09051321B2

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