Formaldehyde → tert-Butyl (3aR*,9bR)-2,3,3a,4,5,5a,9a,9b-octahydro-1H-pyrrolo[3,2-c]quinoline-1-carboxylate

Sodium (1.2 g, 50 mmol) was dissolved in methanol (15 ml), aniline (0.9 g, 10 mmol) was added at room temperature, and the mixture was stirred for 10 min. This mixture was added to a suspension of paraformaldehyde (0.42 g, 14 mmol) in methanol (10 ml), and the mixture was stirred at room temperature for 5 hrs. The reaction mixture was poured into ice water, and the mixture was extracted with diethyl ether. The extract was dried (over anhydrous MgSO4), and the solvent was evaporated under reduced pressure. The residue was dissolved in methanol (20 ml), tert-butyl 2,3-dihydro-1H-pyrrole-1-carboxylate (850 mg, 5 mmol) was added and the mixture was heated under reflux for 18 hrs. The residue was subjected to column chromatography using silica gel (30 g) and eluted with hexane-ethyl acetate (9:1-4:1, v/v) to give the title compound (180 mg, 12%) as an amorphous form.

1. stirringthe mixture was stirred at room temperature for 5 hrs
2. extractionthe mixture was extracted with diethyl ether
3. dry with materialThe extract was dried (over anhydrous MgSO4)
4. customthe solvent was evaporated under reduced pressure
5. dissolutionThe residue was dissolved in methanol (20 ml)
6. temperaturethe mixture was heated
7. temperatureunder reflux for 18 hrs
8. washeluted with hexane-ethyl acetate (9:1-4:1

ORD record

ord-5106d8fc22d4431fa95b832f3725ff80

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07973163B2