Methanol → HCID 13424557, compound

HRID 1389753Notes

Reaction equation

HRID 1389753 reaction equation
O=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].[CH:13]1([NH2:19])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.CO.[H][H]>[Ni].O>[CH:13]1([NH:19][CH2:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

7

Reactant 4

HCID 887MethanolHCID 7965CyclohexylamineHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 178418361HCID 178418361, compound

Product 1

HCID 13424557HCID 13424557, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Procedure

18 G. of D-glucose, 9.9 g. of cyclohexylamine and 1 g. of Raney Nickel in 140 ml. of methanol and 40 ml. of water are treated with hydrogen at 160 psi for 2 hours at 60° C. The solution is filtered to remove the catalyst, and stored overnight at -10° C. to give a precipitate which is recovered by filtration. 2.35 G. of N-cyclohexyl-D-glucamine [m.p. 144°-146° C.; [α]D -20.4° (dimethylsulfoxide)] is obtained.

Workup

  1. filtrationThe solution is filtered
  2. customto remove the catalyst
  3. customto give a precipitate which
  4. filtrationis recovered by filtration

Sources & evidence

ORD record
ord-7772758ec7134f92af88df889135954a
Source dataset
uspto-grants-1981_01
Patent number
US04246193

Reaction notes

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