Cyclohexylamine → HCID 17805634, compound

To a solution of methyl 3-chloro-3-oxopropanoate (2.2 g, 16.1 mmol) in dry DCM (30 ml) at 0° C. was added cyclohexylamine (4.0 g, 40.3 mmol). The reaction mixture was stirred for 1 hr at room temperature. The reaction mixture was washed with diluted HCl, saturated NaHCO3 then brine well. The organic phase was collected, dried over anhydrous sodium sulfate then filtered and concentrated. The resultant crude amide was used directly in the next step with no additional purification (3.2 g, 100%). To a solution of this material (500 mg, 2.51 mmol) in THF/water (1:1, 20 ml) was added NaOH (200 mg, 5.02 mmol) and the mixture was stirred for 3 hrs at room temperature. The mixture was extracted with Et2O then the aqueous phase was acidified to pH 1 and extracted with EtOAc. The organic phase was collected, dried over anhydrous sodium sulfate then filtered and concentrated to afford the title compound 58 as a beige solid (450 mg, 97% yield). MS (m/z): 186.2 (M+H).

1. washThe reaction mixture was washed with diluted HCl, saturated NaHCO3
2. customThe organic phase was collected
3. dry with materialdried over anhydrous sodium sulfate
4. filtrationthen filtered
5. concentrationconcentrated
6. customThe resultant crude amide was used directly in the next step with no additional purification (3.2 g, 100%)
7. stirringthe mixture was stirred for 3 hrs at room temperature
8. extractionThe mixture was extracted with Et2O
9. extractionextracted with EtOAc
10. customThe organic phase was collected
11. dry with materialdried over anhydrous sodium sulfate
12. filtrationthen filtered
13. concentrationconcentrated

ORD record

ord-785e0359193640868cac72a595b98e0d

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08329726B2