Hydrochloric Acid → (3R,5S)-5-(Methoxycarbonyl)pyrrolidin-3-yl 4-vinyl-1,3-dihydro-2H-isoindole-2-carboxylate Hydrochloride

HRID 2377601Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2377601
[CH:1]([C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][N:6]([C:12]([O:14][C@H:15]1[CH2:19][N:18](C(OC(C)(C)C)=O)[C@H:17]([C:27]([O:29][CH3:30])=[O:28])[CH2:16]1)=[O:13])[CH2:7]2)=[CH2:2].[ClH:31]>C(OCC)(=O)C>[ClH:31].[CH:1]([C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][N:6]([C:12]([O:14][C@@H:15]1[CH2:16][C@@H:17]([C:27]([O:29][CH3:30])=[O:28])[NH:18][CH2:19]1)=[O:13])[CH2:7]2)=[CH2:2]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 453783721-t-Butyl 2-methyl (2S,4R)-4-{[(4-vinyl-1,3-dihydro-2H-isoindol-2-yl)carbonyl]oxy}pyrrolidine-1,2-dicarboxylate

Produkt 1

HCID 45379932(3R,5S)-5-(Methoxycarbonyl)pyrrolidin-3-yl 4-vinyl-1,3-dihydro-2H-isoindole-2-carboxylate HydrochlorideAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 1-tert-Butyl 2-methyl (2S,4R)-4-{[(4-vinyl-1,3-dihydro-2H-isoindol-2-yl)carbonyl]oxy}pyrrolidine-1,2-dicarboxylate (13.9 g, 33.4 mmol) in ethyl acetate (700 mL) was cooled in an ice bath the saturated with hydrogen chloride gas. The reaction flask was sealed and allowed to warm to room temperature. After 3.5 h the solvent was removed by evaporation to give the title compound as a gray solid, 11.2 g, 95% yield). 1H NMR (500 MHz, ppm, CD3OD) δ 7.47-7.45 (m, 1 H), 7.32-7.31 (m, 1 H), 7.26-7.21 (m, 1 H), 6.79-6.73 (m, 1 H), 5.79-5.73 (m, 1 H), 5.46 (s, 1 H), 5.41-5.38 (m, 1 H), 4.80-4.72 (m, 4 H), 3.91 (s, 3 H), 3.74-3.63 (m, 2 H), 2.77-2.71 (m, 1 H), 2.51-2.46 (m, 1 H), LRMS (ESI) m/z 317 [(M+H)+; calcd for C17H21N2O4: 317].

Aufarbeitung

  1. customThe reaction flask was sealed
  2. customAfter 3.5 h the solvent was removed by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-698b0bd222404de1a3582664e6085096
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07470664B2

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