Process for producing optically active sulfoxide
An optical and compound technology, applied in the field of preparation of optically active cyclic sulfoxides, can solve problems such as not being suitable for industrial production
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Embodiment 1
[0165] [Example 1] (2S)-spiro[benzo[c]thiophene-1(3H), 4'-piperidine]-1'-tert-butyl formate 2-oxide
[0166] In a nitrogen stream at room temperature, 0.99 ml (3.23 mmol) of titanium (IV) isopropoxide was added dropwise to a mixture of 1.35 ml (6.45 mmol) (-)-diisopropyl tartrate and 40 ml of chlorobenzene. The solution was stirred at room temperature for about 20 minutes, then 0.25 ml (3.22 mmol) of isopropanol was added at room temperature and stirred for a further about 10 minutes. After cooling to below -10°C, 5.00 g (16.2 mmol) of spiro[benzo[c]thiophene-1(3H),4'-piperidine]-1'-carboxylic acid tert-butyl ester was added. A solution of 2.95 ml (17.7 mmol) of cumene hydroperoxide in 10 ml of chlorobenzene was added dropwise below -10°C, and stirred at -10°C for 5 hours. The reaction mixture was analyzed by HPLC, and the mixture contained 86.7% of (2S)-spiro[benzo[c]thiophene-1(3H),4'-piperidine]-1'-carboxylic acid tert-butyl ester 2-oxide, 5.5% spiro[benzo[c]thiophene-1(3...
Embodiment 2
[0169] [Example 2] (2S)-spiro[benzo[c]thiophene-1(3H), 4'-piperidine]2-oxide (S)-(+)-mandelate
[0170] Under a stream of nitrogen, 74.4 g (243.5 mmol) of spiro[benzo[c]thiophene-1(3H), 4'-piperidine]-1'-carboxylic acid tert-butyl ester was mixed with 525 ml of chlorobenzene and added at room temperature 22.8 g (97.4 mmol) (-)-diisopropyl tartrate. Then 7.47 ml (24.3 mmol) of titanium(IV) isopropoxide was added dropwise at room temperature, and the mixture was stirred at the same temperature for about 20 minutes. Then 7.48 ml (97.3 mmol) of isopropanol were added at room temperature and stirred for about 20 minutes. After cooling to below -10°C, a solution of 55.6 g (292.2 mmol) of cumene hydroperoxide in 150 ml of chlorobenzene was added dropwise below -10°C, and stirred at -10°C for 5 hours. The reaction mixture was analyzed by HPLC and the mixture contained 87.3% of (2S)-spiro[benzo[c]thiophene-1(3H),4'-piperidine]-1'-carboxylic acid tert-butyl ester 2-oxide, 3.3% spiro[...
Embodiment 3
[0173] [Example 3] (2S)-spiro[benzo[c]thiophene-1(3H), 4'-piperidine]-1'-methyl carboxylate 2-oxide
[0174] In a nitrogen stream at room temperature, 0.198 ml (0.64 mmol) of titanium (IV) isopropoxide was added dropwise to a mixture of 0.27 ml (1.29 mmol) (-)-diisopropyl tartrate in 9 ml of o-dichlorobenzene. The solution was stirred at room temperature for about 20 minutes, then 49.5 μl (0.64 mmol) of isopropanol was added at room temperature and stirred for about 10 minutes. After cooling to below -10°C, 0.85 g (3.22 mmol) of spiro[benzo[c]thiophene-1(3H),4'-piperidine]-1'-carboxylic acid methyl ester was added. Below -10°C, 0.59ml (3.54mmol) of cumene hydroperoxide in 2ml o-dichlorobenzene was added dropwise, stirred at -10°C for 5 hours, and then the reaction mixture was analyzed by HPLC, the mixture contained 84.7% (2S)- Spiro[benzo[c]thiophene-1(3H), 4'-piperidine]-1'-carboxylic acid methyl ester 2-oxide, 5.9% spiro[benzo[c]thiophene-1(3H), 4 '-Piperidine]-1'-methyl c...
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