Methanol → HCID 20270357, compound

HRID 485369Notes

Reaction equation

HRID 485369 reaction equation
[CH2:1]1[C:8]2[N:4]([C:5]([C:9]([C:11]3[N:12]4[C:16](=[C:17]([C:20]([O:22]CC)=[O:21])[C:18]=3[CH3:19])[CH:15]([C:25]([O:27]CC)=[O:26])[CH2:14][CH2:13]4)=[O:10])=[CH:6][CH:7]=2)[CH2:3][CH2:2]1.CO.[OH-].[K+]>O>[CH2:1]1[C:8]2[N:4]([C:5]([C:9]([C:11]3[N:12]4[C:16](=[C:17]([C:20]([OH:22])=[O:21])[C:18]=3[CH3:19])[CH:15]([C:25]([OH:27])=[O:26])[CH2:14][CH2:13]4)=[O:10])=[CH:6][CH:7]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 13490406HCID 13490406, compound

Product 1

HCID 20270357HCID 20270357, compoundYield 100.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of the diester from Step B (1.62 g, 0.004 m), methanol (15 ml), water (5 ml), and potassium hydroxide (1.6 g, 0.026 m) was refluxed in an inert atmosphere for 5.5 hours, cooled, diluted with water (ca. 80 ml), filtered, the filtrate acidified with 2N hydrochloric acid, and the cooled, aged mixture filtered. After drying the well-washed (water) solid, 1.4 g of 5-(2,3-dihydro-1H-pyrrolizin-5-oyl)-6-methyl-2,3-dihydro-1H-pyrrolizine-1,7-dicarboxylic acid is obtained as a white solid.

Workup

  1. temperaturewas refluxed in an inert atmosphere for 5.5 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. filtrationfiltered
  5. customAfter drying the
  6. washwell-washed (water) solid

Sources & evidence

ORD record
ord-34cbce52408c41a68ff9b5b46897831b
Source dataset
uspto-grants-1985_08
Patent number
US04536512

Reaction notes

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