7,9-Dioxo-6-aza-spiro[3.5]nonane-8-carboxylic acid methyl ester → 6-Azaspiro[3.5]nonane-7,9-dione

HRID 1175169Notes

Reaction equation

HRID 1175169 reaction equation
COC([CH:5]1[C:13](=[O:14])[C:9]2([CH2:12][CH2:11][CH2:10]2)[CH2:8][NH:7][C:6]1=[O:15])=O>C(#N)C.O>[CH2:12]1[C:9]2([C:13](=[O:14])[CH2:5][C:6](=[O:15])[NH:7][CH2:8]2)[CH2:10][CH2:11]1

Participants

3

Reactant 1

HCID 595585517,9-Dioxo-6-aza-spiro[3.5]nonane-8-carboxylic acid methyl ester

Product 1

HCID 595584866-Azaspiro[3.5]nonane-7,9-dione

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

7,9-Dioxo-6-aza-spiro[3.5]nonane-8-carboxylic acid methyl ester (1.30 g, 6.2 mmol) in 30 ml acetonitrile/water (10:1) is refluxed for 1 hour. The reaction mixture is evaporated and the product purified by chromatography on silica. 1H-NMR (400 MHz; DMSO-d6): 8.02 (s, 1H), 3.40 (brs, 2H), 3.25 (s, 2H), 2.30-2.15 (m, 2H), 2.04-1.88 (m, 1H), 1.86-1.70 (m, 3H); LC-MS (m/z, ES+): 153 (MH+), retention time: 0.86 mins (LC-MS method 2)

Workup

  1. customThe reaction mixture is evaporated
  2. customthe product purified by chromatography on silica

Sources & evidence

ORD record
ord-da81d57bbf36482f9b281129b100f94f
Source dataset
uspto-grants-2010_11
Patent number
US07838674B2

Reaction notes

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