Reaktion #91628

ord-28de09a04e584aefb14a1adc9e4ee018

Reaktionsgleichung

[Al+3].[H-].[H-].[H-].[H-].[Li+]
LiAlH4
CCCC(CCC)COc1cccc(C(O)CCNC(=O)OC(C)(C)C)n1
tert-butyl (3-hydroxy-3-(6-((2-propylpentyl)oxy)pyridin-2-yl)propyl)carbamate
CO.ClCCl.N
NH3 MeOH CH2Cl2
→
CCCC(CCC)COc1cccc(C(O)CCNC)n1
3-(methylamino)-1-(6-((2-propylpentyl)oxy)pyridin-2-yl)propan-1-ol

Edukte

—
Example 43
[Al+3].[H-].[H-].[H-].[H-].[Li+]
LiAlH4
CCCC(CCC)COc1cccc(C(O)CCNC(=O)OC(C)(C)C)n1
tert-butyl (3-hydroxy-3-(6-((2-propylpentyl)oxy)pyridin-2-yl)propyl)carbamate
CO.ClCCl.N
NH3 MeOH CH2Cl2

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigegave
  2. 2
    SonstigeYield (0.04 g, 62%)

Vorschrift

LiAlH4 reduction of tert-butyl (3-hydroxy-3-(6-((2-propylpentyl)oxy)pyridin-2-yl)propyl)carbamate following the method described in Example 1 gave after flash chromatography purification (30%-40% 7N NH3/MeOH—CH2Cl2 gradient) Example 43 as a colorless oil; Yield (0.04 g, 62%); 1H NMR (400 MHz, DMSO-d6) δ 7.63 (t, J=8.4 Hz, 1H), 7.03 (d, J=8.0 Hz, 1H), 6.62 (d, J=8.0 Hz, 1H), 4.69-4.66 (m, 1H), 4.18-4.16 (m, 2H), 2.76-2.72 (m, 2H), 2.40 (s, 3H), 2.10-1.68 (m, 3H), 1.46-1.26 (m, 8H), 0.96-0.88 (m, 6H); RP-HPLC tR=10.66 min; ESI-MS m/z 295.3 [M+H]+.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09447078B2uspto-grants-2016_09