Acetic Acid → 1-(Methylcarbonyloxy-methyl)-5-(2-decahydronaphthyl)-spiro[indoline-3,4'-piperidin]-2-one

HRID 1441680Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1441680
COC([CH2:5][N:6]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:8]2([CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[C:7]1=[O:20])=O.[CH2:21]1[CH:30]2[CH:25]([CH2:26][CH2:27][CH2:28][CH2:29]2)[CH2:24][CH2:23][C:22]1=O.[C:32]([OH:35])(=[O:34])[CH3:33].C([BH3-])#N>C1COCC1.ClCCCl>[CH3:33][C:32]([O:35][CH2:5][N:6]1[C:19]2[C:14](=[CH:15][C:16]([CH:22]3[CH2:23][CH2:24][CH:25]4[CH:30]([CH2:29][CH2:28][CH2:27][CH2:26]4)[CH2:21]3)=[CH:17][CH:18]=2)[C:8]2([CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)[C:7]1=[O:20])=[O:34]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 1003282-DecaloneHCID 498716Cyano-borohydrideHCID 591645371-(Methoxycarbonylmethyl)-spiro[indoline-3,4'-piperidin]-2-one

Produkt 1

HCID 685396681-(Methylcarbonyloxy-methyl)-5-(2-decahydronaphthyl)-spiro[indoline-3,4'-piperidin]-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1-(Methoxycarbonylmethyl)-spiro[indoline-3,4′-piperidin]-2-one (0.013 g, 0.049 mmol) was dissolved in dry THF (1.0 mL) and dry 1,2-dichloroethane (0.3 mL). Octahydro-naphthalen-2-one (0.008 g, 0.054 mmol), glacial acetic acid (0.003 g, 0.049 mmol), MP-cyanoborohydride (Polymer support from Argonaut) (0.043 g, 0.099 mmol) were added and the reaction mixture was stirred at room temperature for 18 hrs. The mixture was then filtered, the resin washed with dichloromethane and the solvent evaporated in vacuo to yield the crude compound. The crude compound was purified via flash chromatography (5% methanol/dichloromethane) to yield the title compound as a foam.

Aufarbeitung

  1. filtrationThe mixture was then filtered
  2. washthe resin washed with dichloromethane
  3. customthe solvent evaporated in vacuo
  4. customto yield the crude compound
  5. customThe crude compound was purified via flash chromatography (5% methanol/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-16b619f70a0d4189b576a82578d32524
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07655670B2

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