Hydrochloric Acid → (5S,8S)-methyl-3-(3-chlorophenyl)-2-oxo-1-oxa-3,7-diazaspiro[4.4]nonane-8-carboxylate

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Saturated HCl in MeOH (5 mL) was added to (5S,8S)-di-tert-butyl 3-(3-chlorophenyl)-2-oxo-1-oxa-3,7-diazaspiro[4.4]nonane-7,8-dicarboxylate (107 mg, 0.236 mmol) and stirred at room temp. overnight. The solution was concentrated and chromatography using DCM and 20% MeOH in DCM gave 60 mg (0.193 mmol) of (5S,8S)-methyl-3-(3-chlorophenyl)-2-oxo-1-oxa-3,7-diazaspiro[4.4]nonane-8-carboxylate (B3). 1H NMR (300 MHz, DMSO) 7.68 (s, 1H), 7.6-7.4 (m, 2H), 7.23 (m, 1H), 4.62 (m, 1H), 4.22 (m, 2H), 3.85-3.68 (m, 4H), 3.6-3.5 (m, 1H), 2.9-2.7 (m, 2H). LC MS+: 311.14 at 1.65 min (10-90%, 3-5 min, Formic Acid).

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