Benzaldehyde, 4-octyl- → HCID 178442645, Verbindung

HRID 898212Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 898212
[NH2:1][CH2:2][CH2:3][CH2:4][P:5](C(OCC)OCC)(=[O:9])[O:6]CC.[CH2:17]([C:25]1[CH:32]=[CH:31][C:28]([CH:29]=O)=[CH:27][CH:26]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>CO>[CH2:17]([C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH:1][CH2:2][CH2:3][CH2:4][PH:5](=[O:9])[OH:6])=[CH:27][CH:26]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Komponenten

4

Edukt 2

HCID 2734685Benzaldehyde, 4-octyl-HCID 10422382Phosphinic acid, (3-aminopropyl)(diethoxymethyl)-, ethyl ester

Produkt 1

HCID 178442645HCID 178442645, VerbindungAusbeute 47,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 98.5 mg (0.389 mmol) of ethyl 3-aminopropyl (diethoxymethyl)phosphinate (from Step B) and 84.9 mg (0.389 mmol) of 4-octylbenzaldehyde in 1 mL of MeOH at rt was treated with 12.2 mg (0.194 mmol) Na(CN)BH3. The resulting reaction mixture was stirred at rt for 16 hr. The reaction was quenched with 0.5 mL of 12 N HCl, then heated up to 80° C. for 1 hr. The mixture was cooled and concentrated. HPLC purification (LC-2) afforded 60 mg (47%) of the title compound: 1H NMR (500 MHz, CD3OD) δ 0.88 (t, J=7.1, 3H), 1.25-1.33 (m, 10H), 1.59-1.66 (m, 4H), 1.90-1.96 (m, 2H), 2.63 (t, J=7.7, 2H), 3.09 (t, J=6.9, 2H), 4.12 (s, 2H), 7.03 (d, J=505.6, 1H), 7.27 (d, J=8.0, 2H), 7.38 (d, J=8.0, 2H); LC-1: 3.02 min; ESI-MS 326 (M+H).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. customThe reaction was quenched with 0.5 mL of 12 N HCl
  3. temperatureheated up to 80° C. for 1 hr
  4. temperatureThe mixture was cooled
  5. concentrationconcentrated
  6. customHPLC purification (LC-2)

Quellen und Nachweise

ORD-Eintrag
ord-430a0edb506540d7a71620ba4488423a
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07351725B2

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