Reaktion #693733

ord-4e2f793bc0284991a0cb55c1735977e6

Reaktionsgleichung

CO
methanol
O=C1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
Glucolactone
CNC12C=CC(CC1)C2
Norbornenyl-methylamine
N#CC12C=CC(CC1)C2
norbornene carbonitrile
[Al+3].[H-].[H-].[H-].[H-].[Li+]
LiAlH4
CO
methanol
→
C1=CC2CCC1C2.O=C(O)[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
Norbornene-Gluconate
Ausbeute 70.0%

Edukte

CO
methanol
O=C1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
Glucolactone
CNC12C=CC(CC1)C2
Norbornenyl-methylamine
N#CC12C=CC(CC1)C2
norbornene carbonitrile
[Al+3].[H-].[H-].[H-].[H-].[Li+]
LiAlH4
CO
methanol

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.DISSOLUTIONthe solid does not dissolve initially
  2. 2
    workup.WAITThe reaction proceeded overnight at room temperature
  3. 3
    Sonstigewas removed on a rotary evaporator
  4. 4
    Sonstigethe product was recrystalized from iPrOH/petroleum ether at −4° C. with a yield greater than 70%

Vorschrift

2 ml methanol was added to a 50 ml flask containing 1 g Glucolactone (Aldrich), the solid does not dissolve initially. By the addition of 0.74 g Norbornenyl-methylamine (prepared in lab by the reduction of norbornene carbonitrile with LiAlH4), it disappeared gradually within 20 minutes. The reaction proceeded overnight at room temperature. After the reaction, methanol was removed on a rotary evaporator, and the product was recrystalized from iPrOH/petroleum ether at −4° C. with a yield greater than 70%.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07915318B2uspto-grants-2011_03