Ethyl 2-cyanoethyl(diethoxymethyl)phosphinate → Phosphinic acid, (3-aminopropyl)(diethoxymethyl)-, ethyl ester

HRID 898211Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 898211
[C:1]([CH2:3][CH2:4][P:5]([CH:10]([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])(=[O:9])[O:6][CH2:7][CH3:8])#[N:2]>N.CCO.[Ni]>[NH2:2][CH2:1][CH2:3][CH2:4][P:5]([CH:10]([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])(=[O:9])[O:6][CH2:7][CH3:8]

Komponenten

5

Edukt 1

HCID 10037677Ethyl 2-cyanoethyl(diethoxymethyl)phosphinate

Produkt 1

HCID 10422382Phosphinic acid, (3-aminopropyl)(diethoxymethyl)-, ethyl esterAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 935NickelKatalysatorHCID 222AmmoniaLösungsmittelHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 2.47 g (9.91 mmol) of ethyl 2-cyanoethyl (diethoxymethyl)phosphinate (from Step A) in 20 mL 2.0 M ammonia in EtOH was added 250 mg Raney Nickel. The mixture was subjected to hydrogenation conditions (H2, 40 psi, rt) for 16 hr. The reaction mixture was filtered over Celite and partitioned between CH2Cl2 and H2O. The aqueous phase was extracted twice with CH2Cl2. The organic layer and extractions were combined, dried, and concentrated to provide 2.13 g (85% yield) of the title compound: 1H NMR (500 MHz) δ 1.23 (dt, J1=7.1, J2=1.6 6H), 1.29 (t, J=7.1, 3H), 1.42 (s, br, 2H), 1.71-1.82 (m, 4H), 2.72-2.75 (m, 2H), 3.63-3.70 (m, 2H), 3.78-3.86 (m, 2H), 4.08-4.21 (m, 2H), 4.64 (d, J=6.7, 1H); ESI-MS 254 (M+H).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered over Celite
  2. custompartitioned between CH2Cl2 and H2O
  3. extractionThe aqueous phase was extracted twice with CH2Cl2
  4. extractionThe organic layer and extractions
  5. customdried
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-9dab21afb5be46bab29cb2a1e8c03417
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07351725B2

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