HCID 13537649, compound → HCID 13537649, compound

HRID 638597Notes

Reaction equation

HRID 638597 reaction equation
[O:1]=[C:2]1[NH:6][CH:5]2[CH:7]([CH2:10][C:11]([OH:13])=[O:12])[CH2:8][CH2:9][CH:4]2[CH2:3]1>C(OC(=O)C)(=O)C>[O:1]=[C:2]1[NH:6][CH:5]2[CH:7]([CH2:10][C:11]([OH:13])=[O:12])[CH2:8][CH2:9][CH:4]2[CH2:3]1.[CH2:3]1[CH:4]2[CH2:9][CH2:8][CH:7]3[CH:5]2[N:6]([C:11](=[O:13])[CH2:10]3)[C:2]1=[O:1]

Participants

4

Reactant 1

HCID 13537649HCID 13537649, compound

Product 2

HCID 13537649HCID 13537649, compoundHCID 13537675HCID 13537675, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 1.7 g (0.0092 mol) of octahydro-2-oxocyclopenta[b]pyrrole-6-acetic acid (3aα, 6β, 6aα)] ("cis") and the corresponding "trans" isomer [octahydro-2-oxocyclopenta[b]pyrrole-6-acetic acid (3aα, 6α, 6aα) is prepared in 5.0 g of acetic anhydride. The mixture is stirred and refluxed ten minutes. The acetic acid and unreacted acetic anhydride is removed at reduced pressure and the residue is treated with anhydrous diethyl ether. The residue crystallizes. The desired hexahydro-2H-cyclopenta[gh]pyrrolizine-2,4(1H)-dione (5aα, 7aα, 7bα) is isolated with a melting point of 125°-127° C. after vacuum sublimation. Concentration of the solution yields octahydro-2-oxocyclopenta[b]pyrrole-6-acetic acid (3aα, 6α, 6aα) with a melting point of 230°-232° C.

Workup

  1. temperaturerefluxed ten minutes
  2. customThe acetic acid and unreacted acetic anhydride is removed at reduced pressure
  3. additionthe residue is treated with anhydrous diethyl ether
  4. customThe residue crystallizes

Sources & evidence

ORD record
ord-9970b7000ddb41949b1c94581bae25e8
Source dataset
uspto-grants-1985_12
Patent number
US04562195

Reaction notes

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