Carbon Dioxide → HCID 86695168, compound

Participants

Reaction Steps

Purification of compound 154.1. The racemic 2-[3-chloro-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-12-yl]ethan-1-ol (2.20 g, 8.19 mmol, 1.00 equiv) was resolute by chiral preparative SFC under the following conditions: column: Chiralpak IA, 2*25 cm, 5 um; mobile phase, CO2 (80%), methanol (domestic, 20%); flow rate: 40 g/min; UV detection at 254 nm. The fractions of the first peak to elute (tR=9.28 min) were collected and evaporated under reduced pressure to give the desired 2-[(12S)-3-chloro-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-12-yl]ethan-1-ol (compound 154.1, stereochemistry unconfirmed, 660 mg) as an off-white solid with 100% ee. The fractions of the second peak to elute (tR=10.53 min) were concentrated to give 2-[(12R)-3-chloro-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-12-yl]ethan-1-ol (compound 154.2, stereochemistry unconfirmed, 790 mg) as an off-white solid with 98.5% ee.

Provenance & Evidence