3-Aminopropylphosphonic acid → HCID 44234513, Verbindung

HRID 12546

Reaktionsgleichung

Reaktionsgleichung von HRID 12546
[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([CH:19]=O)=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:21][CH2:22][CH2:23][CH2:24][P:25](=[O:28])([OH:27])[OH:26].[BH3-]C#N.[Na+]>CO>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([CH2:19][NH:21][CH2:22][CH2:23][CH2:24][P:25](=[O:26])([OH:28])[OH:27])=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 975873-Aminopropylphosphonic acidHCID 5003444Sodium cyanoborohydrideHCID 214713565,6-Diphenylpyridine-2-carbaldehyde2×

Produkt 1

HCID 44234513HCID 44234513, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

General Procedure M. To a solution of 5,6-diphenylpyridine-2-carbaldehyde (Compound 54, 95 mg, 0.37 mmol) and (3-amino-propyl)-phosphonic acid (51 mg, 0.37 mmol) in MeOH (3 ml) was added Bu4NOH (0.4 ml, 0.37 mmol, 1M in MeOH) under argon. The mixture was stirred at 50° C. for 30 min. before adding NaCNBH3 (23 mg, 0.37 mmol) to the mixture. The solution was stirred at 50° C. for 3 hours, and then it was concentrated in vacuo. The resulting crude solid was purified MPLC column chromatography (silica gel, 0-100% MeOH in ethyl acetate) to obtain the title compound as a white solid.

Aufarbeitung

  1. stirringThe solution was stirred at 50° C. for 3 hours
  2. concentrationit was concentrated in vacuo
  3. customThe resulting crude solid was purified MPLC column chromatography (silica gel, 0-100% MeOH in ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-eb6ca69b6c7b4a888c638ddbdf043103
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728014B2

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