Methanol → HCID 67068967, compound

HRID 606551Notes

Reaction equation

HRID 606551 reaction equation
[CH2:1]([OH:12])[C@H:2]1[O:8][C:6](=[O:7])[C@H:5]([OH:9])[C@@H:4]([OH:10])[C@@H:3]1[OH:11].[C:13]12(NC)[CH2:19][CH:16]([CH2:17][CH2:18]1)[CH:15]=[CH:14]2.C12(C#N)CC(CC1)C=C2.[H-].[H-].[H-].[H-].[Li+].[Al+3].C[OH:38]>>[O:7]=[C:6]([OH:8])[C@@H:5]([C@H:4]([C@@H:3]([C@@H:2]([CH2:1][OH:12])[OH:38])[OH:11])[OH:10])[OH:9].[CH:13]12[CH2:19][CH:16]([CH2:17][CH2:18]1)[CH:15]=[CH:14]2

Participants

6

Reactant 5

HCID 887Methanol2×HCID 7027delta-GluconolactoneHCID 19737575Bicyclo[2.2.1]hept-2-ene-1-carbonitrileHCID 21226445Aluminium lithium hydrideHCID 57027427HCID 57027427, compound

Product 1

HCID 67068967HCID 67068967, compoundYield 70%

Procedure

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%.

Workup

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

Sources & evidence

ORD record
ord-4e2f793bc0284991a0cb55c1735977e6
Source dataset
uspto-grants-2011_03
Patent number
US07915318B2

Reaction notes

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