Di-tert-butyl dicarbonate → HCID 68557056, Verbindung

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.

1. customto give
2. customisolated)
3. concentrationThe reaction mixture was concentrated under reduced pressure
4. custompurified via chiral preparative HPLC by multiple injections onto Chiralpak AD preparative 250×20 mm (hexane/i-PrOH, 6 ml/min)

ORD-Eintrag

ord-13adc5129e0e43579468efebf4e1c721

Quelldatensatz

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07638517B2