Ammonia → (4R,6R)-tert-Butyl-6-(2-aminoethyl)-2,2-dimethyl-1,3-dioxane-4-acetate

HRID 610636

Reaktionsgleichung

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

Komponenten

Reaktionsbedingungen

Temperatur: 20 °C

Versuchsvorschrift

A solution of (4R-cis)-1,1-dimethylethyl 6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate (Example 5), 8.2 kg (30.5 mol) in 100 L of methanol containing 15 kg of anhydrous ammonia was reacted with hydrogen gas under 50 pounds per square inch (psi) at 30° C. in the presence of a slurry of 8 kg of Raney nickel doped with 1% molybdenum. After 6 hours, uptake of hydrogen had ceased, the mixture was cooled to 20° C., the atmosphere was vented and exchanged for nitrogen, and the slurry was filtered, concentrated by distillation and distilled under vacuum to give 7.8 kg of 96% pure (4R-cis)-1,1-dimethylethyl 6-(2-aminoethyl)-2,2-dimethyl-1,3-dioxane-4-acetate as a clear oil; bp 125-135° C. at 0.5 mm Hg.

Aufarbeitung

filtrationthe slurry was filtered
concentrationconcentrated by distillation
distillationdistilled under vacuum

Quellen und Nachweise

ORD-Eintrag: ord-2ed4ae29f70346828fa8d364a5b4d802
Quelldatensatz: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05998633

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