2-(tert-butoxycarbonyl)-5,7-dichloro-1,2,3,4-tetra

b) A mixture of 1.1 (5 mmol) and 30mmol of LiI in 20mL of pyridine was reflux overnight. The solvent was removed and the residue was dissolved in EtOAc. The resulting solution was then washed with saturated aqueous NH4Cl and dried with anhydrous Na2S04. The solvent was removed and the residue was dried in vacuo to give a quantitative yield of compound 1.3. The crude product was carried on the next step without further purification. ESI-MS (m/z) : (M-tBu +1), 290.[00119] To 1, 2, 3, 4-tetrahydro-6-hydroxy-isoqinoline in acetonitrile was added ptoluenesulfonic acid and N-chlorosuccinimide. The suspension was cooled to ambient temperature, and the product isolated by filtration for a yield of approximately 61percent with purity greater than 95percent. The isolated TsOH salt was recrystallized until purity was greater than 99.7percent. To one equivalent of the TsOH salt suspended in methanol was added 2M sodium carbonate(0.55 eq.) and 1.2 eq. of Boc anhydride. The suspension was stirred at room temperature overnight. The reaction was monitored by HPLC. Upon completion, the mixture was cooled to below 10 °C, water was added, and the Boc-protected dichloro compound was isolated by filtraton. The product was washed and dried at 40 °C for a yield of 95percent and purity of >97percent. The Boc-protected dichloro compound was suspended in dichloromethane (10 volumes) and pyridine(5 volumes) was added. The mixture was cooled to below 2 °C, and triflic anhydride (1.25 eq) was added. The mixture was stirred at 0-2 °C for 10 minutes, and then poured into 10 volumes of 6percent aqueous sodium hydrogen carbonate solution. After washing with dichloromethane, the organic phases were combined and dried over magnesium sulphate. Following purification, the product (Compound 4’) was obtained in 90percent yield and >98percent purity. Compound 4’ was dissolved in dimethylformamide and methanol at room temperature. Diisopropylamine (4 eq) was added. Under CO atmosphere, 1, 3-bis(diphenylphosphino)propane (0.1 eq) and palladium acetate (0.1 eq) was added. The reaction was heated to reflux, and monitored by HPLC. Uponnear completion, the mixture was cooled to ambient temperature. Workup with water, ethyl aceate, and brine yielded Compound 4”, which was used without further purification. Compound 4” was dissolved in methanol and 2.4 M sodium hydroxide (10 volumes each) and refluxed. The mixture was cooled to ambient temperature, and toluene was added. Following aqueous workup, the pH was adjusted to 2.3 with 3M hydrochloric acid, and crude product was isolated byfiltration in 53percent yield with greater than 80percent purity.

Molecular Weight:346.2
XLogP3:3.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:345.0534634
Monoisotopic Mass:345.0534634
Topological Polar Surface Area:66.8
Heavy Atom Count:22
Complexity:451
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes