Hydrochloric Acid → HCID 68541938, compound

Participants

Reaction Conditions

Reaction Steps

Combine 4-(3-tert-butyl-5-iodo-benzyl)-morpholine (0.785 g, 2.2 mmol), benzophenone imine (0.44 mL, 1.2 equiv.), sodium tert-butoxide (0.29 g, 1.4 equiv.), racemic BINAP (0.061 g, 4.5 mol %), and THF (10 mL). De-gas with nitrogen then add bis(dibenzylideneacetone) palladium (0.037 g, 3 mol %) and heat reaction at 50° C. overnight under nitrogen. In the morning add approximately 4 mL of 5 N HCl (aq) and heat for one hour at 50° C. Let cool to room temperature then dilute with ethyl acetate and make basic with 1 N NaOH (aq). Wash organics with water then aqueous saturated sodium chloride. Dry organics with MgSO4, filter and concentrate in vacuo. Purify on silica gel (4:1 Hexanes:Ethyl Acetate→10% Methanol: DCM) to give product (0.449 g, 83%). MS (ES), m/z 249.3 (M+1).

Provenance & Evidence