تفاعل #7913

معادلة التفاعل

thiocarbonyldiimidazole

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

→

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

المردود 64.9%

المذيبات

THF

THF

ظروف التفاعل

المعالجة

1. 1
   workup.WAITat 55° C. for 2 h
2. 2
   درجة الحرارةThe reaction was cooled to room temperature
3. 3
   أخرىmost (˜14 mL) of THF was removed
4. 4
   أخرىThe 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
   درجة الحرارةthe reaction was heated to 45° C. for 8 h
9. 9
   تركيزThe reaction was concentrated to ˜5 mL, and diethyl ether
10. 10
    workup.ADDITIONwas added
11. 11
    أخرىto precipitate product
12. 12
    ترشيحThe product was filtered
13. 13
    غسيلwashed with diethyl ether
14. 14
    أخرىdried

الإجراء التجريبي

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.

المصدر