tert-Butyl 5-((3-(1-admantyl)-4-(octyloxy)phenyl)ethynyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate → 2-Amino-2-(3-(1-admantyl)-4-(octyloxy)phenethyl)propane-1,3-diol

HRID 710462Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 710462
[C:1]12([C:11]3[CH:12]=[C:13]([C:26]#[C:27][C:28]4([NH:36]C(=O)OC(C)(C)C)[CH2:33][O:32]C(C)(C)[O:30][CH2:29]4)[CH:14]=[CH:15][C:16]=3[O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2>CCO.C(C(O)=O)(F)(F)F.[Pd]>[NH2:36][C:28]([CH2:27][CH2:26][C:13]1[CH:14]=[CH:15][C:16]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[C:11]([C:1]23[CH2:2][CH:3]4[CH2:9][CH:7]([CH2:6][CH:5]([CH2:4]4)[CH2:10]2)[CH2:8]3)[CH:12]=1)([CH2:33][OH:32])[CH2:29][OH:30]

Komponenten

5

Edukt 1

HCID 66726408tert-Butyl 5-((3-(1-admantyl)-4-(octyloxy)phenyl)ethynyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

Produkt 1

HCID 461954642-Amino-2-(3-(1-admantyl)-4-(octyloxy)phenethyl)propane-1,3-diolAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6422Trifluoroacetic acidKatalysatorHCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  1. filtrationThe mixture was filtered through Celite bead
  2. washwashed with EtOH (10 ml)
  3. customThe filtrates were evaporated to dryness
  4. dissolutionthe residue was dissolved in MeOH:CH2Cl2 1:1 (5 ml)
  5. addition5 drops of concentrated HCl was added
  6. customsolvents were evaporated to dryness
  7. customThe residue was crystallized from CH3CN

Quellen und Nachweise

ORD-Eintrag
ord-2144458f74b54e618017bf6d9df794ae
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181182B2

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