Methane → HCID 21219056, compound

HRID 2051156Notes

Reaction equation

HRID 2051156 reaction equation
[CH2:1]1[C@H:9]([OH:10])[C@H:8]2[N:3]([CH2:4][C@H:5]([OH:13])[C@@H:6]([OH:12])[C@@H:7]2[OH:11])[CH2:2]1.[CH3:14][C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1.C>N1C=CC=CC=1.O.CO>[CH3:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([O:13][CH:5]2[CH:6]([OH:12])[CH:7]([OH:11])[CH:8]3[N:3]([CH2:2][CH2:1][CH:9]3[OH:10])[CH2:4]2)=[O:20])=[CH:17][CH:16]=1

Participants

7

Reactant 3

HCID 297MethaneHCID 134054-Methylbenzoyl ChlorideHCID 54445Castanospermine

Product 1

HCID 21219056HCID 21219056, compoundYield 12%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To a suspension of 3 g of castanospermine in 30 ml of pyridine at 0° C. was added dropwise a solution of 3 g of 4-methylbenzoyl chloride. After the addition, the mixture wad allowed to warm to room temperature and then heated at 55° C. for 24 hours. The reaction mixture was diluted with 10 ml of water and evaporated to dryness in vacuo. The resulting residue was stirred in 150 ml of a 1:2 mixture of water: methylene chloride. The insoluble material was separated by filtration to provide an amorphous off-white solid which was dissolved in 60 ml of hot methanol, treated with 0.5 g of activated charcoal and filtered. The colorless filtrate was cooled to give colorless crystals of [1S-(1α, 6β, 7α, 8β, 8αβ) ]-octahydro-1,6,7,8-indolizinetetrol 6-(4-methylbenzoate) melting at about 255-258° C. with decomposition (580 mg, 12% yield).

Workup

  1. additionAfter the addition
  2. temperatureheated at 55° C. for 24 hours
  3. customevaporated to dryness in vacuo
  4. customThe insoluble material was separated by filtration
  5. customto provide an amorphous off-white solid which
  6. filtrationfiltered
  7. temperatureThe colorless filtrate was cooled

Sources & evidence

ORD record
ord-a8084b0345ba4ef1a4de282c7065bec7
Source dataset
uspto-grants-1991_05
Patent number
US05017563

Reaction notes

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