Phthalimide → 2-(1-Benzyl-3-methoxymethylpyrrolidin-3-ylmethyl)isoindole-1,3-dione

HRID 729443

Reaktionsgleichung

Reaktionsgleichung von HRID 729443
[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([CH2:16]O)([CH2:13][O:14][CH3:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:37]1(=[O:47])[NH:41][C:40](=[O:42])[C:39]2=[CH:43][CH:44]=[CH:45][CH:46]=[C:38]12.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([CH2:16][N:41]2[C:37](=[O:47])[C:38]3[C:39](=[CH:43][CH:44]=[CH:45][CH:46]=3)[C:40]2=[O:42])([CH2:13][O:14][CH3:15])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 21979083(1-Benzyl-3-methoxymethylpyrrolidin-3-yl)methanol

Produkt 1

HCID 578326372-(1-Benzyl-3-methoxymethylpyrrolidin-3-ylmethyl)isoindole-1,3-dioneAusbeute 21,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of (1-benzyl-3-methoxymethylpyrrolidin-3-yl)methanol (Example A19, 1.71 g, 7.27 mmol), triphenylphosphine (2.16 g, 8.22 mmol), phthalimide (1.14 g, 7.73 mmol), and anhydrous tetrahydrofuran is cooled to 0° C. and treated with diethyl azodicarboxylate (1.62 g, 9.31 mmol). The resulting mixture is stirred at room temperature for 18 hours and concentrated under vacuum. The residue is purified by flash column chromatography (1:5 ethyl acetate/hexanes) to afford the title compound, (0.58 g) as a solid. 1H NMR (200 MHz, CDCl3): δ 7.91-7.80 (m, 2H), 7.78-7.66 (m, 2H), 7.39-7.11 (m, 5H), 3.95-3.72 (m, 2H), 3.65-3.40 (m, 2H), 3.31 (s, 2H), 3.27 (s, 3H), 2.72-2.34 (m, 4H), 2.02-1.82 (m, 1H), 1.76-1.56 (m, 1H). MS ES: m/z 365 (MH+).

Aufarbeitung

  1. customis cooled to 0° C.
  2. concentrationconcentrated under vacuum
  3. customThe residue is purified by flash column chromatography (1:5 ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-c70012a30c4d46d0b299918c255e5ae2
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582627B2

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