ChemicalBook CAS DataBase List Toluene-4-sulfonic acid cis-3-benzyloxycyclobutyl ester

Toluene-4-sulfonic acid cis-3-benzyloxycyclobutyl ester synthesis

8synthesis methods

Product Name:Toluene-4-sulfonic acid cis-3-benzyloxycyclobutyl ester
CAS Number:1262278-62-5
Molecular formula:C18H20O4S
Molecular Weight:332.41

233276-35-2 Synthesis

233276-35-2
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98-59-9 Synthesis

98-59-9
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Toluene-4-sulfonic acid cis-3-benzyloxycyclobutyl ester

1262278-62-5
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Yield:1262278-62-5 98%

Reaction Conditions:

with 4-dimethylaminopyridine in dichloromethane at 0 - 20;

Steps:

Intermediate 13.1 -3-(benzyloxy)cyclobutyl 4-methylbenzenesulfonate

To a solution of (1 s,3s)-3-(benzyloxy)cyclobutan-1 -ol (4 g, 22.44 mmol) in DCM (50 mL) was added DMAP (4.1 1 g, 33.36 mmol). The mixture was cooled to 0 °C and the solution of TsCI (4.71 g, 24.69 mmol) in DCM (30 mL) was added dropwise to the mixture at 0 °C. The mixture was warmed to rt and stirred at rt overnight. The mixture was washed with 1 N HCI (2 x 50 mL) and the aqueous layer was extracted with DCM (2 x 50 mL). The combined organic layers were washed with water and brine, dried over Na₂S0₄ and concentrated to give the title compound (7.3 g, 98%). ¹ H NMR (300 MHz, DMSO-cfe) δ ppm 7.83 (d, 2H), 7.56 - 7.50 (m, 2H), 7.38 - 7.30 (m, 5H), 4.55 (p, 1 H), 4.37 (s, 2H), 3.69 (p, 1 H), 2.61 (ddd, 2H), 2.48 (s, 3H), 2.07 - 1 .93 (m, 2H). LC-MS: [M+H]⁺ = 333.4.

References:

WO2018/234978,2018,A1 Location in patent:Paragraph 00188