Methyl iodide → HCID 178486046, compound

To a suspension of NaH (1.0 g, 41 mmol, 2.5 equiv) in DMF (30 mL) at −10° C. was added cis-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)cyclohexanecarboxylic acid (4.0 g, 16 mmol, 1.0 equiv). The reaction mixture was allowed to warm to room temperature and then was stirred for 1 h. The mixture was again cooled to −10° C., and MeI (25 g, 260 mmol, 16 equiv) was added dropwise. The cold bath was removed, and the reaction mixture was stirred for 3 h at room temperature. The mixture was poured onto ice, and then NaOH (1.5 g) was added to hydrolyze any undesired methyl ester that formed. This solution was stirred for another 4 hours. The aqueous layer was washed with ethyl acetate and concentrated under reduced pressure to remove the DMF. The resulting residue was diluted with water, and the pH was adjusted to ˜3-4. The desired product precipitated as a white solid which was collected by filtration (2.5 g).

1. temperatureThe mixture was again cooled to −10° C.
2. customThe cold bath was removed
3. stirringthe reaction mixture was stirred for 3 h at room temperature
4. additionThe mixture was poured onto ice
5. additionNaOH (1.5 g) was added
6. customthat formed
7. stirringThis solution was stirred for another 4 hours
8. washThe aqueous layer was washed with ethyl acetate
9. concentrationconcentrated under reduced pressure
10. customto remove the DMF
11. additionThe resulting residue was diluted with water
12. customThe desired product precipitated as a white solid which
13. filtrationwas collected by filtration (2.5 g)

ORD record

ord-14fd39bfad704959a9c4649e3c645fe5

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08173805B2