4-Toluenesulfonyl chloride → HCID 86632370, compound

Participants

Reaction Steps

Et3N (2.56 mL, 18.4 mmol) and DMAP (153 mg, 1.23 mmol) were added to a sol. of [2-chloro-5-(2-hydroxy-ethyl)-benzyl]-cyclopropyl-carbamic acid tert-butyl ester (4.00 g, 12.3 mmol) in CH2Cl2 (110 mL) at 0° C. A sol. of p-toluenesulfonyl chloride (2.80 g, 14.7 mmol) in CH2Cl2 (18 mL) was added dropwise, and the mixture was stirred for 3 days while warming up to rt. The mixture was partitioned between CH2Cl2 and water, and the aq. layer was extracted with CH2Cl2 (3×). The combined org. layers were washed with brine, dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (heptane/EtOAc 8:2) yielded the title compound (4.90 g, 83%). LC-MS: tR=1.13 min; ES+: 480.53.

Provenance & Evidence