P,P-Diphenylphosphinic azide → HCID 16244434, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of XXXIII (1 g, 4.2 mmol) and TEA (1 mL) in 10 mL of tert-butylalcohol was added 1.15 g of diphenyl phosphoryl azide (4.2 mol). The reaction mixture was stirred at 80° C. for 12 h before concentrated in vacuo. The residue was dissolved in 20 mL of HCl/MeOH (1 N) and the mixture was stirred for at rt for 2 h. After solvent removal, the residue was partitioned between water and EtOAc. The aqueous layer was neutralized to pH 8 by addition of Na2CO3, and extracted with EtOAc. The organic phase was dried over Na2SO4 and concentrated to give 0.25 g of 3-amino-chroman-6-carboxylic acid methyl ester XXXIV (Yield 29%). MS: calc'd 208 (MH+), exp 208 (MH+).

Provenance & Evidence