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Step 9-2: Production of (R)-1-(tert-butoxycarbonyl)-3-dimethylaminopyrrolidine To 1.25 g of (R)-1-(tert-butoxycarbonyl)-3-dimethylaminopyrrolidine hydrochloric acid salt (chemical purity: 99.9 areapercent) obtained in the step 9-1 were added 2.46 g of a 23percent by weight brine, 5.03 g of toluene and 738 mg of a 30percent by weight aqueous sodium hydroxide solution, and the mixture was stirred. After conducting liquid separation, the organic layer was concentrated. Then vacuum drying was carried out to give the title compound as 999 mg of a colorless and transparent liquid (chemical purity: 99.5 areapercent, yield 95percent). 1H-NMR (CDCl3): d (ppm) 1.46 (s, 9H), 1.74 (m, 1H), 2.05 (m, 1H), 2.24 (s, 6H), 2.63 (m, 1H), 3.05 (m, 1H), 3.27 (m, 1H), 3.45-3.69 (m, 2H)
Step 9-2: Production of (R)-1-(tert-butoxycarbonyl)-3-dimethylaminopyrrolidine To 1.25 g of (R)-1-(tert-butoxycarbonyl)-3-dimethylaminopyrrolidine hydrochloric acid salt (chemical purity: 99.9 area%) obtained in the step 9-1 were added 2.46 g of a 23% by weight brine, 5.03 g of toluene and 738 mg of a 30% by weight aqueous sodium hydroxide solution, and the mixture was stirred. After conducting liquid separation, the organic layer was concentrated. Then vacuum drying was carried out to give the title compound as 999 mg of a colorless and transparent liquid (chemical purity: 99.5 area%, yield 95%). 1H-NMR (CDCl3): d (ppm) 1.46 (s, 9H), 1.74 (m, 1H), 2.05 (m, 1H), 2.24 (s, 6H), 2.63 (m, 1H), 3.05 (m, 1H), 3.27 (m, 1H), 3.45-3.69 (m, 2H)
With sodium cyanoborohydride; magnesium sulfate; acetic acid; In methanol; at 20.0℃; for 24.0h;
To a dried 100mL single-mouth round bottom flask were added absolute methanol (40 mL), (R)-butyl 3-aminopyrrolidine-1-carboxylate (1.86g, 1.0mmol), paraformaldehyde(3g), anhydrous magnesium sulfate (2.5g), acetic acid (1.2g) and sodium cyanoborohydride (2.5g, 39.8mmol). The mixture was stirred at room temperature for 24 hr. The reaction system was poured into water to quench, The solution was concentrated under reduced pressure and the residue was extracted with ethyl acetate. The combined organ layer was dried, and was concentrated under reduced pressure to obtain a crude yellow viscous product (3.8g).
With hydrogenchloride; In dichloromethane; for 3.0h;
In a dried reaction flask, the crude (R)-butyl 3-(dimethylamino)pyrrolidine-1-carboxylate (2.0g) obtained in the above step was added to CH2Cl2 (30mL). HCl gas was passed thereto for 3 h. The solution was concentrated under reduced pressure to obtain a crude yellow viscous material (1.5g).
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