Acetone Cyanohydrin → tert-butyl (1S)-1-[cyano(hydroxy)methyl]pentylcarbamate
Reaktionsgleichung
[CH3:1][C:2]([O:5][C:6]([NH:8][C@@H:9]([CH2:12][CH2:13][CH2:14][CH3:15])[CH2:10][OH:11])=[O:7])([CH3:4])[CH3:3].CC(C)(O)[C:18]#[N:19].C(N(CC)CC)C>>[OH:11][CH:10]([C@@H:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:12][CH2:13][CH2:14][CH3:15])[C:18]#[N:19]Komponenten
4
Versuchsvorschrift
40 g (200 mmol) of (S)-2-[N-(2-methyl-2-propyloxycarbonyl)amino]hexanol was dissolved in 300 ml of anhydrous methylenechroride, 34 g (400 mmol) of acetone cyanhydrin and 12.1 g (120 mmol) of triethylamine were added to the above-prepared reaction solution, followed by stirring for one night. The reaction solution was concentrated under reduced pressure. The residue thus obtained was washed with 300 ml of ether in addition to distilled water and dried over anhydride sodium sulfate and concentrated under reduced pressure. The residue was separated out by silica gel column chromatography, whereby 38.7 g of (2RS,3S)-2-hydroxy-3-[N-(2-methyl-2-propyloxycarbonyl)amino]heptanenitrile was obtained.