Methanol → Dimethyl 3-aminopentanedioate

HRID 1741190

Reaktionsgleichung

Reaktionsgleichung von HRID 1741190
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5](=O)[CH2:6][C:7]([O:9][CH3:10])=[O:8].CO.C([O-])=O.[NH4+].[BH3-]C#[N:21].[Na+]>Cl.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:12])[CH2:4][CH:5]([NH2:21])[CH2:6][C:7]([O:9][CH3:10])=[O:8]

Komponenten

7

Edukt 4

HCID 887MethanolHCID 74591Dimethyl 3-oxoglutarateHCID 2723923Ammonium formateHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 253304Dimethyl 3-aminopentanedioateAusbeute 75,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Dimethyl-3-oxoglutarate (10 g, 57 mmol) was added to methanol (225 ml) followed by ammonium formate (36 g, 570 mmol) and NaBH3CN (3.7 g, 57 mmol) at 25° C. After 24 h, the methanol was removed in vacuo to leave a white mass. Methylene chloride was added and the mixture filtered. The methylene chloride was evaporated resulting in an oil which was dissolved in 1N HCl (200 ml) and extracted with ether (100 ml). The ether layer was discarded and the aqueous layer was made basic using solid K2CO3. The product was extracted into methylene chloride, dried over Na2SO4, and evaporated to give dimethyl-3-aminoglutarate (7.5 g). 1H NMR (d6-DMSO) δ 1.76 (bs, 2H), 2.45 (dd, 4H, J=8.1 Hz, 16.6 Hz), 3.69 (s, 6H), 5.45 (m, 1H); MS (FAB) m/z 176.0 (MH+).

Aufarbeitung

  1. customthe methanol was removed in vacuo
  2. customto leave a white mass
  3. filtrationthe mixture filtered
  4. customThe methylene chloride was evaporated
  5. customresulting in an oil which
  6. extractionextracted with ether (100 ml)
  7. extractionThe product was extracted into methylene chloride
  8. dry with materialdried over Na2SO4
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-eef5dfda739648a7b82ac5c576274171
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05973003

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