Hydrochloric Acid → HCID 22002639, compound

Participants

Reaction Steps

To the alcohol from Step 2 (924 mg, 3.91 mmol) in 10 mL CH2Cl2 at 0° C. was added pyridine (928 mg, 11.7 mmol) followed by phenylacetyl chloride (1.51 g, 9.77 mmol). The ice bath was removed and the mixture was stirred at room temperature for 15 h. Aq. NH4Cl (100 mL) was added and the mixture was extracted with EtOAc (3×50 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated. The residue was dissolved in 16 mL CH2Cl2, DBU (595 mg, 3.91 mmol) was added and the brown solution was stirred at room temperature for 0.5 h. 5% aq. HCl (100 mL) was added and the mixture was extracted with EtOAc (4×50 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated to give 1.40 g (quantitative) of the title compound as a yellow solid, used directly in the next step. An analytical sample had mp. 147-148° C. after stirring with Et2O/hexane (2:1).

Provenance & Evidence