Sodium Bicarbonate → tert-Butyl (3R)-4-Hydroxy-3-phenylmethylbutanoate
Reaktionsgleichung
[C:1]([O:5][C:6]([CH2:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])(O)=O.[Na+]>O1CCCC1>[OH:11][CH2:10][C@H:9]([CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH2:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To the resultant acid from Example 99 (1.03 g, 3.90 mmol) in tetrahydrofuran (4 ml, THF) at 0° C. was added BH3 in THF (5.8 ml, 5.8 mmol, 1.0 molar) over 2 min. After 2 h at 0° C. the mixture was brought to room temperature and stirred for 2 h. The reaction was poured into saturated NaHCO3 solution and extracted into ethyl acetate which was dried over Na2SO4 and evaporated. Chromatography of the residue on silica gel with ethyl acetate/hexane mixtures afforded 0.55 g (56%) of the desired product as an oil. 1H NMR (CDCl3, TMS) δ 7.15-7.35 (m,5H), 3.65 (m,1H), 3.52 (m,1H), 2.65 (m,2H), 2.30 (m,2H), 1.90 (m,1H), 1.46 (s,9H).