1,6-Dioxaspiro[2.5]octane → HCID 59255048, Verbindung

HRID 1809345Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1809345
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:3][CH2:2]1.[O:19]1[C:21]2([CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[CH2:20]1>CO>[OH:19][C:21]1([CH2:20][N:1]2[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:3][CH2:2]2)[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1

Komponenten

4

Edukt 2

HCID 1604391,6-Dioxaspiro[2.5]octaneHCID 14809798Benzyl (piperidin-4-ylmethyl)carbamate

Produkt 1

HCID 59255048HCID 59255048, VerbindungAusbeute 49,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of benzyl (piperidin-4-ylmethyl)carbamate (7.77 g, 31.3 mmol, prepared according to Bose, D. Subhas et al., Tetrahedron Lett., 1990, 31, 6903) and 1,6-dioxaspiro[2.5]octane (4.29 g, 37.6 mmol, prepared according to Satyamurthy, Nagichettiar et al., Phosphorus Sulfur, 1984, 19, 113) in methanol (93 mL) was stirred at room temperature for 20 h. Then, the mixture was refluxed for 8 h. After cooling to room temperature, the solvent was removed in vacuo. The residue was chromatographed on a column of silica gel eluting with dichloromethane/methanol (v/v=20/1) to give 5.60 g (49%) of the title compound as colorless oil.

Aufarbeitung

  1. temperatureThen, the mixture was refluxed for 8 h
  2. temperatureAfter cooling to room temperature
  3. customthe solvent was removed in vacuo
  4. customThe residue was chromatographed on a column of silica gel eluting with dichloromethane/methanol (v/v=20/1)

Quellen und Nachweise

ORD-Eintrag
ord-b2612b5d28144a91bc773913dc8ae9b8
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362038B2

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