Trifluoroacetic acid → HCID 55296257, compound

To a solution of [2-(tetrahydro-pyran-4-ylamino)-ethyl]-carbamic acid tert-butyl ester (6.60 g, 27.0 mmol) in DCM (100 mL) was added triethylamine (11.3 mL, 81.1 mmol) followed by chloroacetyl chloride (3.64 g, 32.4 mmol) dropwise. The reaction mixture was stirred at RT for 24 h, then partitioned between DCM and saturated NaHCO3 aqueous solution. The organic layer was isolated, dried (Na2SO4) and concentrated in vacuo. To a solution of the resulting residue in THF (50 mL) was added sodium hydride (60% in mineral oil) (1.62 g, 40.6 mmol). The reaction mixture was stirred at RT for 20 h, then partitioned between DCM and water. The organic layer was dried (Na2SO4) and concentrated in vacuo to yield an orange residue. The residue (7.66 g, 27.0 mmol) was dissolved in dichloromethane (15 mL) and TFA (15 mL) was added. The resulting solution was stirred at RT for 4 h before being concentrated in vacuo. The resultant residue was loaded onto an Isolute® SCX-2 cartridge, washed with MeOH then eluted with 2 M NH3 in MeOH to give the title compound as yellow oil (4.26 g, 86%).

1. custompartitioned between DCM and saturated NaHCO3 aqueous solution
2. customThe organic layer was isolated
3. dry with materialdried (Na2SO4)
4. concentrationconcentrated in vacuo
5. stirringThe reaction mixture was stirred at RT for 20 h
6. custompartitioned between DCM and water
7. dry with materialThe organic layer was dried (Na2SO4)
8. concentrationconcentrated in vacuo
9. customto yield an orange residue
10. stirringThe resulting solution was stirred at RT for 4 h
11. concentrationbefore being concentrated in vacuo
12. washwashed with MeOH
13. washthen eluted with 2 M NH3 in MeOH

ORD record

ord-813c2d2c4e2843b682b5f3f82f48fac6

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08293735B2