4-Chlorobenzoyl chloride → tert-Butyl 2-(4-(3-(4-chlorophenyl)-3-oxopropanoyl)phenyl)morpholine-4-carboxylate

Temperature

-78 °C

tert-Butyl 2-(4-acetylphenyl)morpholine-4-carboxylate (210 mg, 0.69 mmol) was dissolved in THF (3.5 ml). Lithium-bis-(trimethylsilyl)-amide solution (2.05 ml, 2.05 mmol, 1.0 M solution in THF) was added dropwise and the yellow reaction mixture was stirred at −78° C. for 1 hour. 4-Chlorobenzoyl chloride (120 mg, 0.69 mmol) was added and the reaction mixture was stirred for 90 min and was quenched by addition of 1M aqueous hydrochloric acid. Ethyl acetate was added and the organic layer was dried over MgSO4 and evaporated. The crude material was purified by flash chromatography (10 g silica gel, 10 to 50% ethyl acetate in heptane) to yield an off-white solid (215 mg, 70%). MS (ISP): 388.2 ([{35Cl}M-tBu+H]+), 390.3 ([{37Cl}M-tBu+H]+).

1. stirringthe reaction mixture was stirred for 90 min
2. customwas quenched by addition of 1M aqueous hydrochloric acid
3. additionEthyl acetate was added
4. dry with materialthe organic layer was dried over MgSO4
5. customevaporated
6. customThe crude material was purified by flash chromatography (10 g silica gel, 10 to 50% ethyl acetate in heptane)

ORD record

ord-ae9c480ffaaa497b92be4b038445ee85

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181230B2