Reaktion #797644

Reaktionsgleichung

product

tert-Butyl 5-((3-(1-admantyl)-4-(octyloxy)phenyl)ethynyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

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titled compound

Ausbeute 81.0%

2-Amino-2-(3-(1-admantyl)-4-(octyloxy)phenethyl)propane-1,3-diol

Ausbeute 81.0%

Lösungsmittel

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe mixture was filtered through Celite bead
2. 2
   Waschenwashed with EtOH (10 ml)
3. 3
   SonstigeThe filtrates were evaporated to dryness
4. 4
   workup.DISSOLUTIONthe residue was dissolved in MeOH:CH2Cl2 1:1 (5 ml)
5. 5
   workup.ADDITION5 drops of concentrated HCl was added
6. 6
   Sonstigesolvents were evaporated to dryness
7. 7
   SonstigeThe residue was crystallized from CH3CN

Vorschrift

A slurry of the product of Step B (0.04 g, 0.068 mmol) and 10% Pd/C (0.04 g) in a mixture of EtOH: CF3CO2H (10 ml: 2 drops) was stirred for 36 h under H2. The mixture was filtered through Celite bead and washed with EtOH (10 ml). The filtrates were evaporated to dryness and the residue was dissolved in MeOH:CH2Cl2 1:1 (5 ml) and 5 drops of concentrated HCl was added. The mixture was stirred for 1 h and solvents were evaporated to dryness. The residue was crystallized from CH3CN to give the titled compound (0.025 g, 81%) as colourless powder. 1H-NMR (CDCl3) 0.79 (t, 3H, J=6.57 Hz); 1.12-1.21 (m, 7H); 1.37-1.41 (m, 2H); 1.69 (s, 6H); 1.73-1.88 (m, 3H); 2.00 (b, 9H); 2.48-2.52 (m, 2H); 3.61 (d, 2H, J=11.84 Hz); 3.67 (d, 2H, J=12.2 Hz); 3.85 (tr, 2H, J=6.22 Hz); 6.69 (d, 1H, J=8.13 Hz); 6.88-7.93 (m, 2H).

Quelle