Ammonia → HCID 15045168, Verbindung

HRID 1198359

Reaktionsgleichung

Reaktionsgleichung von HRID 1198359
[C:1]([CH2:3][C@H:4]1[O:9][C:8]2([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[O:7][C@@H:6]([CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:5]1)#[N:2].N.[H][H]>CO.O>[NH2:2][CH2:1][CH2:3][C@H:4]1[O:9][C:8]2([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[O:7][C@@H:6]([CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:5]1

Komponenten

6

Edukt 3

HCID 222AmmoniaHCID 15045166(+/-)-cis-1,1-Dimethylethyl 4-(cyanomethyl)-1,5-dioxaspiro[5.5]undecane-2acetateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 15045168HCID 15045168, VerbindungAusbeute 97,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 1.19 g of (±)-cis-1,1-dimethylethyl 4-(cyanomethyl)-1,5-dioxaspiro[5.5]undecane-2-acetate in 30 mL of methanol saturated with gaseous ammonia is treated with 0.3 g of Raney nickel #30 and hydrogen gas in a shaker at 60 pounds per square inch gage (psig) and 40° C. After 22 hours, thin layer chromatography indicates no starting nitrile present. The suspension is cooled, filtered through filter aid, and concentrated to an oil. This crude oil is purified by silica gel flash chromatography (30:20:1; ethyl acetate:methanol:ammonium hydroxide) to give 1.18 g of (±)-cis-1,1-dimethylethyl 4-(2-aminoethyl)- 1,5-dioxaspiro[5.5]undecane-2-acetate as a clear oil which solidifies upon standing.

Aufarbeitung

  1. temperatureThe suspension is cooled
  2. filtrationfiltered
  3. filtrationthrough filter aid
  4. concentrationconcentrated to an oil
  5. customThis crude oil is purified by silica gel flash chromatography (30:20:1; ethyl acetate:methanol:ammonium hydroxide)

Quellen und Nachweise

ORD-Eintrag
ord-a27d9e68b10e48b4a192ef42afc95934
Quelldatensatz
uspto-grants-1994_01
Patentnummer
US05280126

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