反应 #164001

反应方程式

2-(tert-Butoxycarbonylamino-methyl)-8-(2-dimethylamino-vinyl)-10,10-dimethyl-10H-pyrido[1,2-a]indolylium perchlorate

hydroxylamine-O-sulfonic acid

Sodium bicarbonate

→

2-(tert-Butoxycarbonylamino-methyl)-8-cyanomethyl-10,10-dimethyl-10H-pyrido[1,2-a]indolylium perchlorate

溶剂

MeOH—H2O

反应条件

后处理

1. 1
   其他equipped with magnetic stir bar
2. 2
   workup.DISSOLUTIONIn about 2 hours all solid was dissolved
3. 3
   workup.STIRRINGstirring
4. 4
   其他was evaporated under vacuum
5. 5
   其他The product deposited on flask
6. 6
   洗涤the deposited tar was washed with water (2*60 mL)
7. 7
   workup.DISSOLUTIONdissolved in 250 mL water-methanol (1:1) mixture
8. 8
   其他Most of the solvent was again removed in vacuum, aqueous solution (approximately 50 mL)
9. 9
   洗涤the separated organic residue was washed with water (2*60 mL), ether
10. 10
    其他dried
11. 11
    其他The crude product was used in the next step without additional purification

实验过程

2-(tert-Butoxycarbonylamino-methyl)-8-(2-dimethylamino-vinyl)-10,10-dimethyl-10H-pyrido[1,2-a]indolylium perchlorate (14 g, 0.028 mol; Sigma-Aldrich) was placed into 500-mL conical flask equipped with magnetic stir bar followed by 400 mL of 1:1 MeOH—H2O mixture. Stirring was started and hydroxylamine-O-sulfonic acid (14 g, 0.12 mol; Aldrich) was added to the flask in one portion. In about 2 hours all solid was dissolved and stirring was continued for additional 48 hours at room temperature. Sodium bicarbonate (2.00 g) was added to the reaction mixture to adjust pH equal to 7.0. The reaction mixture was transferred into 1-L round bottom one-necked flask and 80% of the reaction solvent was evaporated under vacuum. The product deposited on flask wall as a slightly yellow tar. The aqueous solution (ca 80-100 mL) that contained excess of hydroxylalamino sulfonic acid was discarded and the deposited tar was washed with water (2*60 mL) and dissolved in 250 mL water-methanol (1:1) mixture. Most of the solvent was again removed in vacuum, aqueous solution (approximately 50 mL) discarded, the separated organic residue was washed with water (2*60 mL), ether and dried. The crude product was used in the next step without additional purification. The yield of crude material was 13.1 g (100% of theory).

来源