Triethylamine → Methyl 1-aminospiro(2.2)pentane-1-carboxylate hydrochloride

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Reaction Steps

To a mixture of spiro[2.2]pentane-1,1-dicarboxylic acid methyl ester (400 mg, 2.30 mmol) in 3 mL of anhydrous t-BuOH was added 700 mg (2.50 mmol) of DPPA and 278 mg (2.70 mmol) of Et3N. The mixture was heated at reflux for 21 h and then partitioned between H2O and ether. The ether phase was dried over magnesium sulfate, filtered and concentrated in vacuo to yield an oil. To this oil was added 3 mL of a 4 M HCl/dioxane solution. This acidic solution was stirred at rt for 2 h and then concentrated in vacuo. The residue was triturated with ether to give 82 mg (20%) of 1-amino-spiro[2.2]pentane-1-carboxylic acid methyl ester hydrochloride salt as a white solid. 1H NMR (300 MHz, CDCl3) δ 9.19 (br s, 3H), 3.81 (s, 3H), 2.16, (d, J=5.5 Hz, 1H), 2.01 (d, J=5.5 Hz, 1H), 1.49 (m, 1H), 1.24, (m, 1H), 1.12 (m, 2H). LRMS of free amine: MS m/z 142 (M++1)

Provenance & Evidence