Acetic Anhydride → 2,4-Dioxo-3-oxa-9-aza-bicyclo[3.3.1]nonane-9-carboxylic Acid Benzyl Ester

HRID 987079Notes

Reaction equation

HRID 987079 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH:16]([C:17]([OH:19])=[O:18])[CH2:15][CH2:14][CH2:13][CH:12]1[C:20](O)=[O:21])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC(=O)C)(=O)C>>[CH2:1]([O:8][C:9]([N:11]1[CH:16]2[CH2:15][CH2:14][CH2:13][CH:12]1[C:20](=[O:21])[O:18][C:17]2=[O:19])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 12265926Piperidine-1,2,6-tricarboxylic acid 1-benzyl ester2×

Product 1

HCID 544831212,4-Dioxo-3-oxa-9-aza-bicyclo[3.3.1]nonane-9-carboxylic Acid Benzyl EsterYield 100%

Conditions

Temperature
70 °C

Procedure

Piperidine-1,2,6-tricarboxylic acid 1-benzyl ester (Compound 1, 19.7 g, 64.11 mmol) was suspended in acetic anhydride (80 mL, 848 mmol) in a dry 250-mL round-bottom flask. The mixture was stirred at 70° C. for 30 minutes until a clear solution formed. The remaining acetic anhydride was removed in vacuo, to afford Compound 2 (18.5 g, 100%) as a clear oil. The material was of sufficiently good quality to be used in the next reaction without purification. The product was sensitive to water, so it was prepared for immediate use in the next step. 1H NMR: δ 1.57-2.01 (cm, 6H), 5.14 (s, 2H), 5.17 (s, 2H), 7.32-7.37 (m, 5H).

Workup

  1. customformed
  2. customThe remaining acetic anhydride was removed in vacuo

Sources & evidence

ORD record
ord-9f2feb5bf69c4b21a4699eb958f2d07f
Source dataset
uspto-grants-2003_10
Patent number
US06630472B1

Reaction notes

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