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trans-4-(tert-butoxycarbonylamino)cyclohexyl 4-methylbenzenesulfonate synthesis

2synthesis methods
-

Yield:957035-42-6 83%

Reaction Conditions:

with N,N-dimethyl-4-aminopyridine;triethylamine in dichloromethane at 18 - 25; for 24 h;Inert atmosphere;

Steps:

9 Preparation of [trans-4-(tert-butoxycarbonylamino)cyclohexyl] 4-methylbenzenesulfonate:

TsCl (8.50 g, 44.1 mmol) was added to a stirred solution of BOC-trans-4-aminohexanol (5.00 g, 22.0 mmol) in DCM (20 mL), followed by TEA (9.32 mL, 66.2 mmol) and DMAP (275 mg, 2.21 mmol). After 24 h stirring, the solid was filtered off, the solution was concentrated and the residue was purified by column chromatography (silica gel; PE:EA; 1:1; v:v) to afford [trans-4-(tert-butoxycarbonylamino)cyclohexyl] 4-methylbenzenesulfonate as a light yellow solid (7.5 g, 83% yield).1H NMR (400 MHz, DMSO-d6) δ ppm: 7.79 (d, J = 8.0 Hz, 2H), 7.46 (d, J = 8.0 Hz, 2H), 6.71 (d, J = 7.2 Hz, 1H), 4.34 (m, 1H), 3.20 (m, 1H), 2.41 (s, 3H), 1.73 (m, 4H), 1.46 (m, 2H), 1.35 (s, 9H), 1.18 (m, 2H).

References:

WO2022/74143,2022,A1 Location in patent:Page/Page column 83

224309-64-2 Synthesis
4-N-BOC-AMINO-CYCLOHEXANOL

224309-64-2
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1024015-36-8 Synthesis
CarbaMic acid, N-[cis-4-[[(4-Methylphenyl)sulfonyl]oxy]cyclohexyl]-, 1,1-diMethylethyl ester

1024015-36-8
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