Tetrahydrofuran-3-YL 4-methylbenzenesulfonate, (3R)- → (+)-7-Chloro-6-(tetrahydrofuran-3-ylthio)-2,3,4,5-tetrahydro-1H-benzo[d]azepine Hydrochloride

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Reaction Steps

Use a method similar to the Example 332, using 3-tert-butoxycarbonyl-7-chloro-6-dimethylcarbamoylthio-2,3,4,5-tetrahydro-1H-benzo[d]azepine and (R)-toluene-4-sulfonic acid tetrahydro-furan-3-yl ester to give, after deprotection using a method similar to the General Procedure 1-4, the title compound as an off-white solid. MS (APCI+) m/z: 284 (M+H); [α]20D +32.5° (c 0.5, CH3OH); ee=95.7% [Chiral HPLC: Column: YMC ODS-AQ 120 Å 4.6×50 mm [S-3 μm]; eluent: gradient from 95:5 to 5:95 A/B; solvent A: water, 0.01% HFBA, 10% isopropanol; solvent B: acetonitrile, 0.01% HFBA, 1% isopropanol; flow rate 2 mL/min].

Provenance & Evidence