Cesium carbonate → HCID 59299494, compound

Participants

Reaction Conditions

Reaction Steps

Place Pd2(dba)3 (710 mg, 3.16 mmol), BINAP (2.95 g, 4.74 mmol), and Cs2CO3 (15.0 g, 47.0 mmol) in a dry flask. Add 3,5-dichloro-4-((1-cyclohexyl-2-oxopyrrolidin-3-yl)methyl)phenyl trifluoromethanesulfonate (Example 240) (15.0 g, 32.0 mmol), benzophenone imine (8.60 g, 47.4 mmol), and 750 mL of toluene. Heat at 100° C. overnight. Cool to room temp and filter. Remove toluene under reduced pressure. Dissolve crude imine in MeOH and add sodium acetate (5.20 g, 63.0 mmol) and hydroxylamine hydrochloride (4.40 g, 63.0 mmol). Stir at room temp for 45 min. Pour into water and extract with CH2Cl2. Dry, filter, and concentrate. Purify the residue by Biotage eluting with a mixture of EtOAc and hexanes (30:70 to 50:50) to give the title compound (7.0 g, 65%): Mass spectrum (apci) m/z=341.2 (M+H).

Provenance & Evidence