[OH2:1].Cl.O[NH2:4].C(=O)([O-])[O-].[Na+].[Na+].[O:11]1[C:15]2([CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[O:14][CH2:13][C@@H:12]1[CH:21]=O>C1COCC1>[O:11]1[C:15]2([CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[O:14][CH2:13][C@@H:12]1[CH:21]=[N:4][OH:1]To 1000 mL of DI water was added hydroxyl amine hydrochloride (51.0 g, 734 mmol) and the mixture was stirred for 5 minutes. Sodium carbonate (38.1 g, 360 mmol) was added in 3 large portions and the reaction was stirred for 15 minutes. THF (700 mL) was added to the reaction and (R)-1,4-dioxaspiro[4.5]decane-2-carbaldehyde (125 g, 734 mmol) in 800 mL of THF was added in 1 portion. The reaction was stirred for 4 hours and poured into a 4 L separatory funnel and the layers were separated. The aqueous layer was extracted twice with MTBE (about 3000 mL total). The combined organic layers were washed with water (700 mL) and brine (300 mL), dried over MgSOa, and concentrated in vacuo to afford (S)-1,4-dioxaspiro[4.5]decane-2-carbaldehyde oxime (135 g, 99%) as a clear viscous oil.
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