Sodium Hydroxide → N,N-dimethyl-O-(9-phenyl-9H-fluoren-9-yl)-L-serine
Reaktionsgleichung
C[O:2][C:3](=[O:29])[C@H:4]([CH2:8][O:9][C:10]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:22]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:5]([CH3:7])[CH3:6].[OH-].[Na+]>CO>[CH3:6][N:5]([CH3:7])[C@H:4]([C:3]([OH:29])=[O:2])[CH2:8][O:9][C:10]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:22]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of 0.39 g (1 mmol) N,N-Dimethyl--O--(9-phenyl-9H-fluoren-9-yl)-L-serine methyl ester from Step 1 in methanol (4 mL) was added 20% sodium hydroxide (2 mL) and the mixture stirred at room temperature for 1 h. Most of the methanol was evaporated in vacuo, the residue suspended in water (10 mL) and extracted with diethyl ether (2×2 mL). The alkaline aqueous phase was acidified with 20% acetic acid by cooling with an ice bath, the white precipitate was filtered, washed with water and dried in vacuo over P2O5 to give 0.314 g (yield 84%) N,N-dimethyl-O-(9-phenyl-9H-fluoren-9-yl)-L-serine as a white powder. 1H NMR (CD3OD, 300 MHz) δ: 7.87 (br s, 2H), 7.70-7.10 (m, 11H), 3.70-3.45 (m, 3H), 2.95 (s, 6H).