Trimethylaluminum → HCID 68869399, compound

To a 2M solution of trimethylaluminum in dichloromethane (30 mL) was added slowly a solution of methyl N-(3-aminopropyl)-N-(tert-butoxycarbonyl)-D-alaninate (11.5 g) in dichloromethane. The reaction mixture was stirred at room temperature for four days and then poured into a flask containing 30 g of Celite. The mixture was stirred and quenched by the slow addition of about 10 mL of saturated aqueous ammonium chloride solution. Sodium sulfate (20 g) and methanol (50 mL) were added. The mixture was stirred for 1 h, then filtered. The solids were washed with 5% methanol/dichloromethane. The filtrate was concentrated. The residue was purified by flash chromatography (silica gel, eluting sequentially with 4, 6, 7 and 12% of 10:1 methanovaqueous concentrated ammonium hydroxide in dichloromethane) to provide the title compound containing less than 3% of the (3S)-isomer. MS 228.9 (M+1).

1. additionpoured into a flask
2. additioncontaining 30 g of Celite
3. stirringThe mixture was stirred
4. customquenched by the slow addition of about 10 mL of saturated aqueous ammonium chloride solution
5. additionSodium sulfate (20 g) and methanol (50 mL) were added
6. stirringThe mixture was stirred for 1 h
7. filtrationfiltered
8. washThe solids were washed with 5% methanol/dichloromethane
9. concentrationThe filtrate was concentrated
10. customThe residue was purified by flash chromatography (silica gel
11. washeluting sequentially with 4, 6, 7 and 12% of 10:1 methanovaqueous concentrated ammonium hydroxide in dichloromethane)

ORD record

ord-fcd9673c80ed4365948bb26683344a3f

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07560455B2