n-Cbz-(1r)-1-[(rs)-(5-tert-butyl-2-benzoxazolyl)hydroxymethyl]-3-phenylpropylamine → (1R)-1-[(RS)-(5-tert-Butyl-2-benzoxazolyl)hydroxymethl]-3-phenylpropylamine
Reaktionsgleichung
C([NH:11][C@@H:12]([CH:21]([C:23]1[O:24][C:25]2[CH:31]=[CH:30][C:29]([C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:28][C:26]=2[N:27]=1)[OH:22])[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(OCC1C=CC=CC=1)=O>[Pd].CO>[C:32]([C:29]1[CH:30]=[CH:31][C:25]2[O:24][C:23]([CH:21]([OH:22])[C@H:12]([NH2:11])[CH2:13][CH2:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[N:27][C:26]=2[CH:28]=1)([CH3:35])([CH3:33])[CH3:34]Komponenten
4
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
A mixture of N-CBz-(1R)-1-[(RS)-(5-tert-butyl-2-benzoxazolyl)hydroxymethyl]-3-phenylpropylamine (360 mg), anhydrous methanol (8 ml), and 10% palladium-on-charcoal (40 mg) was degassed, under reduced pressure, and then stirred vigorously under hydrogen atmosphere for 10 h. The mixture is filtered on a nylon pad (0.45 pm porosity) and concentrated in vacuo to afford the title product (210 mg) as a clear oil: 1H NMR (400 MHz, CDCl3, 3:2 mixture of diastereomers) δ1.80-2.02 (m, 2H), 2.65-2.89 (m, 2H), 3.23 (m, 0.4H), 3.39 (m, 0.6H), 4.76 (d, J=1.8 Hz, 0.6H), 4.84 (d, J=2.4 Hz, 0.4H), 7.09 (m, 3H), 7.29 (m, 2H), 7.43 (m, 2H), and 7.76 (s, 1H).