Potassium Carbonate → Benzyl 2-(aminomethyl)morpholine-4-carboxylate

HRID 1371379Notes

Reaction equation

FC(F)(F)C([NH:5][CH2:6][CH:7]1[O:12][CH2:11][CH2:10][N:9]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:8]1)=O.C(=O)([O-])[O-].[K+].[K+]>CO.O>[NH2:5][CH2:6][CH:7]1[O:12][CH2:11][CH2:10][N:9]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:8]1

Participants

Conditions

Temperature: 22 °C

Procedure

To a stirred solution of Intermediate 4 (4.4 g) in 1:1 methanol/water (300 ml) was added potassium carbonate (17.5 g). The mixture was stirred at 22° C. for 36 h before the volatiles were evaporated in vacuo. The residue was dissolved in water and the solution extracted with dichloromethane (×3). The combined organic extracts were washed with saturated aqueous sodium chloride solution, dried over magnesium sulphate and filtered before evaporation of the solvent in vacuo. The residue was dissolved in methanol and purified by solid phase extraction (Isolute SCX sulphonic acid column), initially washing the cartridge with methanol before eluting with 10% 0.880 ammonia solution in methanol to give the title compound as a colourless oil (2.27 g).

Workup

customwere evaporated in vacuo
dissolutionThe residue was dissolved in water
extractionthe solution extracted with dichloromethane (×3)
washThe combined organic extracts were washed with saturated aqueous sodium chloride solution
dry with materialdried over magnesium sulphate
filtrationfiltered before evaporation of the solvent in vacuo
dissolutionThe residue was dissolved in methanol
custompurified by solid phase extraction (Isolute SCX sulphonic acid column)
washinitially washing the cartridge with methanol
washbefore eluting with 10% 0.880 ammonia solution in methanol

Sources & evidence

ORD record: ord-bc0c9e0f44a347829666ad9d82382715
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07157457B2

Reaction notes

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