Methanol → Methyl 2-oxospiro[indoline-3,4'-piperidine]-5-carboxylate hydrochloride

HRID 390165Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 390165
C(OC([N:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:22]([OH:24])=[O:23])[CH:20]=3)[NH:15][C:14]2=[O:25])[CH2:10][CH2:9]1)=O)(C)(C)C.O=S(Cl)[Cl:28].[CH3:30]O>>[ClH:28].[O:25]=[C:14]1[C:11]2([CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([C:22]([O:24][CH3:30])=[O:23])[CH:20]=2)[NH:15]1

Komponenten

4

Edukt 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 497601931'-(Tert-butoxycarbonyl)-2-oxospiro[indoline-3,4'-piperidine]-5-carboxylic acid

Produkt 1

HCID 67223037Methyl 2-oxospiro[indoline-3,4'-piperidine]-5-carboxylate hydrochlorideAusbeute 81 %

Versuchsvorschrift

To a solution of 1′-(tert-butoxycarbonyl)-2-oxospiro[indoline-3,4′-piperidine]-5-carboxylic acid (2 g, 6.0 mmol) in methanol (30 mL) was added dropwise SOCl2 (5 mL) at 0° C. Then the reaction mixture was stirred overnight at rt. The reaction mixture was concentrated to give methyl 2-oxospiro[indoline-3,4′-piperidine]-5-carboxylate hydrochloride (1.4 g, 81%), which was used for the next step without purification. 1H NMR (CD3OD): 2.00 (m, 2H), 2.20 (m, 2H), 3.281 (m, 1H), 3.39 (m, 2H), 3.61 (m, 2H), 3.85 (m, 2H), 3.88 (m, 2H), 7.00 (m, 1H), 7.98 (m, 2H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-332cae25456343b58a77f49bc41abff3
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383629B2

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