Dimethyl Sulfoxide → HCID 58786478, compound

Temperature

-78 °C

To DMSO (2.19 mL) in MeCl2 (40 mL) at −78° C. was added (COCl)2 (1.29 mL, ×mmol) dropwise. The reaction mixture was allowed to stir at −78° C. for 15 minutes and then 4-(2-Hydroxy-1-phenyl-ethyl)piperazine-1-carboxylic acid tert-butyl ester (364) (3.78 g, 12.34 mmol) in MeCl2 (8 mL) was added. The reaction mixture was allowed to stir at −78° C. for 1 h and then TEA (8.6 mL) amine added. The reaction mixture was allowed to stir at −78° C. for another 3 h and then allowed to warm to room temperature and stirred for 18 h. The reaction mixture is then quenched with sat. NH4Cl (55 mL). The desired product is extracted into EtOAc (100 mL). The organic phase is dried over MgSO4 and concentrated to dryness. The crude material was purified by chromatography (silica gel 60 mesh, eluting with 30% EtOAc in hexanes) yielding 2.37 g (63%) pure product.

1. stirringto stir at −78° C. for 1 h
2. stirringto stir at −78° C. for another 3 h
3. temperatureto warm to room temperature
4. stirringstirred for 18 h
5. customThe reaction mixture is then quenched with sat. NH4Cl (55 mL)
6. extractionThe desired product is extracted into EtOAc (100 mL)
7. dry with materialThe organic phase is dried over MgSO4
8. concentrationconcentrated to dryness
9. customThe crude material was purified by chromatography (silica gel 60 mesh, eluting with 30% EtOAc in hexanes)

ORD record

ord-9ff52cf69d0c4c98a7e0cf9487c37d3e

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07169777B2