反応 #75557

反応方程式

thiocarbonyldiimidazole

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

→

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

収率 64.9%

溶媒

THF

THF

反応条件

後処理

1. 1
   workup.WAITat 55° C. for 2 h
2. 2
   温度The reaction was cooled to room temperature
3. 3
   その他most (˜14 mL) of THF was removed
4. 4
   その他The 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
   温度the reaction was heated to 45° C. for 8 h
9. 9
   濃縮The reaction was concentrated to ˜5 mL, and diethyl ether
10. 10
    workup.ADDITIONwas added
11. 11
    その他to precipitate product
12. 12
    ろ過The product was filtered
13. 13
    洗浄washed with diethyl ether
14. 14
    その他dried

実験手順

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.

出典