Acetic Anhydride → HCID 131714479, compound

HRID 638599Notes

Reaction equation

HRID 638599 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=[C:11]([CH2:12][C:13]([OH:15])=O)[C:2]1=2.C(OC(=O)C)(=[O:18])C>>[CH2:4]1[C:3]2=[CH:6][CH:7]=[CH:8][CH:9]=[CH:10][C:11]3=[C:2]2[N:1]([C:13](=[O:15])[CH2:12]3)[C:5]1=[O:18]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 54737984HCID 54737984, compound2×

Product 1

HCID 131714479HCID 131714479, compound

Procedure

A solution of ±1H-cycloocta[b]pyrrole-9-acetic acid, decahydro-2-oxo-, (3aα, 9β, 9aα)-; ±1H-cyloocta[b]pyrrole-9-acetic acid,decahydro-2-oxo, (3aα, 9α, 9aα)-; ±1H-cycloocta[b]pyrrole-9-acetic acid, decahydro-2-oxo-, (3aα, 9β, 9aβ) (2.8 g, 0.012 mol) in acetic anhydride is heated at reflux for 30 minutes and allowed to cool to room temperature overnight. The solution is concentrated at reduced pressure and the resulting solid is triturated with anhydrous diethyl ether. Sublimation (120° C., 0.1 mm) yields cycloocta[gh]pyrrolizine-2,4-(1H, 5H)-dione, octahydro-, (5aα, 10a α, 10bα)-; ±cycloocta[gh]pyrrolizine-2,4(1H,5H)-dione, octahydro-, (5aβ, 10aβ, 10bα)-; cycloocta[gh]pyrrolizine-2,4(1H,5H)dione,octahydro-, (5aα, 10aβ, 10bα)- with mp 121°-124° and 132°-134° C.

Workup

  1. temperatureat reflux for 30 minutes
  2. concentrationThe solution is concentrated at reduced pressure
  3. customthe resulting solid is triturated with anhydrous diethyl ether

Sources & evidence

ORD record
ord-a5168b115bd247069921cf405146158a
Source dataset
uspto-grants-1985_12
Patent number
US04562195

Reaction notes

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