Sodium hydride → HCID 70896185, compound

To a stirred solution of (S)-(−)-3-aminoquinuclidine dihydrochloride (0.2 g, 0.8 mmol) in methylene chloride (2 mL) was added sodium hydride (0.1 g, 1.6 mmol) and the mixture was stirred for 2 h. A solution of methyl 1-(2-oxoethyl)-1H-benzo[d]imidazole-7-carboxylate (0.2 g, 0.7 mmol) from Step E above in methylene chloride (3 mL) was added followed by acetic acid (0.7 mL) and the mixture was stirred at room temperature for 4 h. Sodium triacetoxyborohydride (0.4 g, 2.1 mmol) was then added in portions and the reaction was stirred at room temperature overnight. The crude reaction was quenched with methanol, concentrated under reduced pressure, and purified by preparative thin layer chromatography (90:9:1 methylene chloride/methanol/ammonium hydroxide) to afford (S)-methyl 1-(2-(quinuclidin-3-ylamino)ethyl)-1H-benzo[d]imidazole-7-carboxylate (0.2 g, quantitative yield): MS (ESI+) m/z 329 (M+H).

1. stirringthe mixture was stirred at room temperature for 4 h
2. stirringthe reaction was stirred at room temperature overnight
3. customThe crude reaction
4. customwas quenched with methanol
5. concentrationconcentrated under reduced pressure
6. custompurified by preparative thin layer chromatography (90:9:1 methylene chloride/methanol/ammonium hydroxide)

ORD record

ord-9b29908babb640daaad3093063da1a55

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09045501B2