Diisopropylethylamine → (S)-3-(tert-butyldiphenylsilyloxy)-N1-(1-adamantylmethyl)propane-1,2-diamine

To a solution of (S)-2-amino-3-((1-adamantylmethyl)amino)propan-1-ol HCl salt (1.2 g, 3.8 mmol) in anhydrous CH2Cl2 (20 mL) were added DIEA (1.9 g, 15.2 mmol), DMAP (2.3 mg, 0.02 mmol) and TBDPSCl (1.2 g, 4.2 mmol) at 0° C. The mixture was stirred at rt for 2 h. The reaction solution was extracted with CH2Cl2 (100 mL) and water (20 mL). The organic layer was washed with brine (20 mL), dried over MgSO4, and concentrated to give the crude product, which was purified by preparative TLC (PE:EtOAc 10/1) to afford (S)-3-(tert-butyldiphenylsilyloxy)-N1-(1-adamantylmethyl)propane-1,2-diamine (620 mg, 29%) 1H NMR: (CDCl3, 400 MHz): δ=1.05 (s, 9H), 1.54 (s, 6H), 1.62-1.73 (m, 6H), 1.98 (s, 3H), 2.32 (d, 1H), 2.45 (d, 1H), 2.56 (d, 1H), 2.85 (d, 1H), 3.15 (m, 4H), 3.65 (m, 2H), 7.4 (m, 6H), 7.62 (m, 4H).

1. extractionThe reaction solution was extracted with CH2Cl2 (100 mL) and water (20 mL)
2. washThe organic layer was washed with brine (20 mL)
3. dry with materialdried over MgSO4
4. concentrationconcentrated
5. customto give the crude product, which
6. customwas purified by preparative TLC (PE:EtOAc 10/1)

ORD record

ord-c3e7ace0c19f4e1d9e9d57f0aadba26a

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08835426B2