Dimethylformamide → HCID 71264777, compound

Participants

Reaction Steps

To a 0° C. solution of R-5 (15 mmol, 3.0 g) in THF (50 mL) is added methylmagnesium chloride (1.5M in THF, 18 mmol, 12 mL). The solution is stirred for 5 min then treated with a solution of n-BuLi (2.6M in hexanes, 45 mmol, 18 mL). The solution is stirred for 5 min then treated with DMF (150 mmol, 11.0 g). The cold bath is removed and the mixture is stirred for 10 min then treated with water, extracted with CH2Cl2 and filtered through a phase separator. The filtrate is concentrated in vacuo to give R-7 (2.20 g, 99%). To a solution of R-7 (14.5 mmol, 2.20 g) and morpholine (44 mmol, 38.00 g) in DCE (dichloroethane) (150 mL) is added sodium triacetoxyborohydride (73 mmol, 15.50 g). The mixture is stirred at 60° C. for 24 h then cooled to ambient temperature and poured into 20% (w/w) aqueous Na2CO3 and extracted with 10% methanol in CH2Cl2. The organics are collected, dried over MgSO4, filtered, and concentrated in vacuo. The residue is purified by flash chromatography to give the title intermediate (2.50 g, 76%).

Provenance & Evidence