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650579-38-7

4-Morpholinecarboxylic acid, 2-(chloromethyl)-, 1,1-dimethylethyl ester synthesis

2synthesis methods
24424-99-5 Synthesis
Di-tert-butyl dicarbonate

24424-99-5
832 suppliers
$13.50/25G

2-(chloromethyl)morpholine

122894-70-6
17 suppliers
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Yield:650579-38-7 283 mg

Reaction Conditions:

in methanol at 20; for 5 h;

Steps:

26

A solution of 2-(chloromethyl)-4-(phenylmethyl)morpholine (498 mg, 2.21 mmol) in methanol (20 mL) was hydrogenated over 10% Pd-C (120 mg) for 17 h. The catalyst was filtered off, and the filtrate was concentrated to give 2-(chloromethyl)morpholine as a colorless oil. To a solution of this oil in methanol (20 mL) was added di-tert-butyl dicarbonate (425 mg, 1.95 mmol), and the reaction mixture was stirred at room temperature for 5 h. Concentration and purification by column chromatography on silica (9:1 hexanes/ethyl acetate) provided 1,1-dimethylethyl 2-(chloromethyl)morpholine-2-carboxylate 283 mg (54%) as a colorless solid. 1H NMR (400 MHz, d4-MeOH): 4.02 (d, 1H), 3.88 (d, 1H), 3.81 (m, 1H), 3.61-3.47 (m, 4H), 2.95 (br. s, 1H), 2.75 (br. s, 1H), 1.46 (s, 9H).

References:

US2016/129032,2016,A1 Location in patent:Paragraph 0515