Methanol → 875467-74-6

Temperature

0 °C

1.9 g of (R)-(+)-4-chloromandelonitrile (11 mmol) were dissolved in 18 ml THF and cooled down to 0° C. under nitrogen. 58 ml of a 1M borane-THF complex solution in THF were then added dropwise over 30 min, keeping the temperature between 0-2° C. After addition the reaction mixture was stirred at rt for additional 45 min and then refluxed for 16 h. The reaction mixture is then cooled down to 0° C. and treated between 2 and 5° C. with 13 ml methanol over a period of 35 min. After 1 h refluxing the reaction mixture is concentrated, the residue dissolved in DCM and the amine extracted twice with 1N aqueous HCl. The combined aqueous phases are then treated with concentrated NaOH to adjust the pH to 12, and then extracted twice with DCM. The combined organic phases were then washed with water, dried over magnesium sulfate, filtered and concentrated in vacuo leading to a colorless solid which was dissolved in 100 ml diethylether, treated with 4 ml 2.6N HCl in diethylether, stirred at rt for additional 1 h, filtered and dried under high vacuo, leading to 1.24 g white solid (54%). MS (ISP) 172.1 (M+H)+.

1. custombetween 0-2° C
2. additionAfter addition the reaction mixture
3. temperaturerefluxed for 16 h
4. temperatureThe reaction mixture is then cooled down to 0° C.
5. temperatureAfter 1 h refluxing the reaction mixture
6. concentrationis concentrated
7. dissolutionthe residue dissolved in DCM
8. extractionthe amine extracted twice with 1N aqueous HCl
9. additionThe combined aqueous phases are then treated with concentrated NaOH
10. extractionextracted twice with DCM
11. washThe combined organic phases were then washed with water
12. dry with materialdried over magnesium sulfate
13. filtrationfiltered
14. concentrationconcentrated in vacuo
15. dissolutionwas dissolved in 100 ml diethylether
16. additiontreated with 4 ml 2.6N HCl in diethylether
17. stirringstirred at rt for additional 1 h
18. filtrationfiltered
19. customdried under high vacuo

ORD record

ord-6c16017d4ac54da9bb8dcd220240c3a9

Source dataset

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07259183B2