تفاعل #693733

ord-4e2f793bc0284991a0cb55c1735977e6

معادلة التفاعل

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
المردود 70.0%

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

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

الإجراء التجريبي

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%.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07915318B2uspto-grants-2011_03