2,2,4,4-Tetramethylthietan-3-one → 3-Amino-2,2,4,4-tetramethylthietane

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Reaction Steps

The 2,2,4,4-tetramethylthietan-3-one of Example 9, Step 1a, was converted to the corresponding oxime using hydroxylamine hydrochloride and sodium acetate by the procedure described in Example 12B of U.S. Pat. No. 4,411,925. The oxime (12.0 g., 0.045 moles) in 50 ml. of THF was added dropwise to a stirred suspension of LiAlH4 (6 g., 0.15 moles) in 50 ml. of THF at 0° C. After addition of the oxime was completed, the reaction mixture was allowed to warm to room temperature and was then refluxed for 1.5 hours. The reaction was carefully quenched by dropwise addition of 6 ml. of H2O, 6 ml. of 15% NaOH and 18 ml. of H2O. The quenched solution was filtered and the filtrate evaporated to give 8 g. of crude amine. The crude amine was purified by silica gel chromatography with 5% methanol/chloroform as the eluting solvent. Yield: 3.8 l g.

Provenance & Evidence