Di-tert-butyl dicarbonate → HCID 68557056、化合物
反応式
CNCCC(C1C=CC=CC=1)C1C2C(=NC=CC=2)NC=1.CC(OC(OC(OC(C)(C)C)=O)=O)(C)C.[C:36]([O:40][C:41](=[O:62])[N:42]([CH3:61])[CH2:43][CH2:44][CH:45]([C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)[C:46]1[C:54]2[C:49](=[N:50][CH:51]=[CH:52][CH:53]=2)[NH:48][CH:47]=1)([CH3:39])([CH3:38])[CH3:37]>C(Cl)Cl>[C:36]([O:40][C:41](=[O:62])[N:42]([CH3:61])[CH2:43][CH2:44][C@H:45]([C:55]1[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=1)[C:46]1[C:54]2[C:49](=[N:50][CH:51]=[CH:52][CH:53]=2)[NH:48][CH:47]=1)([CH3:39])([CH3:38])[CH3:37]参加物
5
実験手順
To a 0° C. solution of racemic methyl-[3-phenyl-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)-propyl]-amine (267 mg, 1.01 mmol) in DCM (40 ml) was added TEA (0.47 ml, 3.37 mmol) followed by Boc2O (416 mg, 1.91 mmol). The mixture was warmed to RT over 1 hour, and then stirred at RT for 22 hours to give a racemic mixture of Methyl-[3-phenyl-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)-propyl]-carbamic acid tert-butyl ester (not isolated). The reaction mixture was concentrated under reduced pressure, and purified via chiral preparative HPLC by multiple injections onto Chiralpak AD preparative 250×20 mm (hexane/i-PrOH, 6 ml/min), affording (R)-Methyl-[3-phenyl-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)-propyl]-carbamic acid tert-butyl ester (215 mg, 31% yield) as a first fraction and (S)-Methyl-[3-phenyl-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)-propyl]-carbamic acid tert-butyl estere (197 mg, 28% yield) as a second fraction.