반응 #75557

반응 방정식

thiocarbonyldiimidazole

methylpyrrolidin-3-yl-carbamic acid tert-butyl ester

→

methyl-(1-thiocarbamoyl-pyrrolidin-3-yl)-carbamic acid tert-butyl ester

수율 64.9%

용매

THF

THF

반응 조건

후처리

1. 1
   workup.WAITat 55° C. for 2 h
2. 2
   온도The reaction was cooled to room temperature
3. 3
   기타most (˜14 mL) of THF was removed
4. 4
   기타The reaction was transferred to a sealable reaction tube
5. 5
   workup.ADDITION2N ammonia in methanol (6 mL) was added
6. 6
   workup.STIRRINGthe reaction was stirred at room temperature overnight
7. 7
   workup.ADDITIONAnother portion of 2N ammonia in methanol (6 mL) was added
8. 8
   온도the reaction was heated to 45° C. for 8 h
9. 9
   농축The reaction was concentrated to ˜5 mL, and diethyl ether
10. 10
    workup.ADDITIONwas added
11. 11
    기타to precipitate product
12. 12
    여과The product was filtered
13. 13
    세척washed with diethyl ether
14. 14
    기타dried

실험 절차

To a stirring solution of thiocarbonyldiimidazole (1.23 g, 6.91 mmol) in THF (10 mL) under N2 was added methylpyrrolidin-3-yl-carbamic acid tert-butyl ester (1.20 g, 5.99 mmol) in THF (7 mL). The reaction mixture was stirred at room temperature of 1 h, and then at 55° C. for 2 h. The reaction was cooled to room temperature, and most (˜14 mL) of THF was removed. The reaction was transferred to a sealable reaction tube, 2N ammonia in methanol (6 mL) was added, and the reaction was stirred at room temperature overnight. Another portion of 2N ammonia in methanol (6 mL) was added, and the reaction was heated to 45° C. for 8 h. The reaction was concentrated to ˜5 mL, and diethyl ether was added to precipitate product. The product was filtered, washed with diethyl ether, and dried to obtain 0.920 g (64.9%) of pure methyl-(1-thiocarbamoyl-pyrrolidin-3-yl)-carbamic acid tert-butyl ester (132) as a white solid.

출처