Hydrogen oxalate monoanion → 2-Dimethylamino-1-[spiro(cyclopentane-1,1'-indene)-3'-yl]ethanol

HRID 1856284Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1856284
[CH3:1][N:2]([CH3:20])[C:3](=O)[C:4](=[O:18])[C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]2([CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:6]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O)(=O)C([O-])=O>C(OCC)C.C(#N)C>[CH3:1][N:2]([CH3:20])[CH2:3][CH:4]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]2([CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:6]=1)[OH:18]

Komponenten

6

Edukt 3

HCID 3716971Hydrogen oxalate monoanionHCID 21226445Aluminium lithium hydrideHCID 23346446HCID 23346446, Verbindung

Produkt 1

HCID 233464542-Dimethylamino-1-[spiro(cyclopentane-1,1'-indene)-3'-yl]ethanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittel2×HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

The oxoamide from step (a) (2.69) in anhydrous diethyl ether (200 ml) is stirred for 24 hours at about 20° C. with lithium aluminium hydride (2 g) in diethyl ether (100 ml). The excess of hydride is destroyed with saturated aqueous sodium sulphate solution. The ether phase is separated, washed, dried and concentrated to an oil which contains 2-dimethylamino-1-[spiro(cyclopentane-1,1'-indene)-3'-yl]ethanol contaminated by much of the corresponding indanyl analogue. The two compounds are separated by chromatography on aluminium oxide with diethyl ether/methanol as eluent. The product so obtained is converted into the hydrogen oxalate of the title compound in acetonitrile solution. M.p. 133°-134° C.

Aufarbeitung

  1. customThe excess of hydride is destroyed with saturated aqueous sodium sulphate solution
  2. customThe ether phase is separated
  3. washwashed
  4. customdried
  5. concentrationconcentrated to an oil which
  6. customThe two compounds are separated by chromatography on aluminium oxide with diethyl ether/methanol as eluent
  7. customThe product so obtained

Quellen und Nachweise

ORD-Eintrag
ord-752f413907e34c63b35e5db58f10cc94
Quelldatensatz
uspto-grants-1980_08
Patentnummer
US04218472

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