5-methoxy-3,4-dihydro-2H-pyrrole

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A slurry of 3.0 g (0.0152 mole) of powdered 2-phenylcyclopentylamine hydrochloride and 3 ml of O-methylbutyrolactim is allowed to stand at room temperature with occasional stirring for 6 days after which the material is covered with absolute ether. The solution is allowed to stand at room temperature for an additional 6 days. A precipitate forms which is collected and recrystallized from acetone-methanol and dried to give 2-[(2-phenylcyclopentyl)imino]pyrrolidine hydrochloride, M.P. 155°-158° C. to stand at room temperature to stand at room temperature for an additional 6 days A precipitate forms which is collected recrystallized from acetone-methanol dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A slurry of 3.0 g (0.0152 mole) of powdered 2-phenylcyclopentylamine hydrochloride and 3 ml of O-methylbutyrolactim is allowed to stand at room temperature with occasional stirring for 6 days after which the material is covered with absolute ether. The solution is allowed to stand at room temperature for an additional 6 days. A precipitate forms which is collected and recrystallized from acetone-methanol and dried to give 2-[(2-phenylcyclopentyl)imino]pyrrolidine hydrochloride, M.P. 155°-158° C. to stand at room temperature to stand at room temperature for an additional 6 days A precipitate forms which is collected recrystallized from acetone-methanol dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Substituting this amine for the α-methyl-ρ-phenethylbenzylamine hydrochloride, and substituting O-methylbutyrolactim for the O-methylcaprolactim results in the formation of 2-[α-methyl-m-(4-phenoxybutoxy)benzylimino]pyrrolidine hydrochloride, having a M.P. of 136°-8° C. (dec.)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Substituting this amine for the α-methyl-ρ-phenethylbenzylamine hydrochloride, and substituting O-methylbutyrolactim for the O-methylcaprolactim results in the formation of 2-[α-methyl-m-(4-phenoxybutoxy)benzylimino]pyrrolidine hydrochloride, having a M.P. of 136°-8° C. (dec.)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Triethylamine (0.5 mL, 3.6 mmol) was added to a mixture of dimethyl 1,3-acetonedicarboxylate (16.3 mL, 111 mmol) and 5-methoxy-3,4-dihydro-2H-pyrrole (10 g, 101 mmol), and the reaction stirred for 72 h. The white solid was collected by filtration, rinsed with ether, and dried under vacuum to give 15.8 g (75%) of compound 1a. 1H NMR (400 MHz, DMSO-d6): δ 11.11 (s, 1H), 5.54 (s, 1H), 3.94 (t, 2H, J=7.6 Hz), 3.80 (s, 3H), 3.36 (t, 2H, J=7.6 Hz), 2.02-2.11 (m, 2H). MS (ES) [m+H] calc'd for C10H11NO4, 210. found 210. The white solid was collected by filtration rinsed with ether dried under vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 5-Methoxy-3,4-dihydro-2H-pyrrole (5.35 g, 54.0 mmol), isopropylidene malonate (7.78 g, 54.0 mmol), triethylamine (1.35 mL, 9.7 mmol) and benzene (55 mL) is refluxed under nitrogen overnight. The reaction is cooled to RT and concentrated and the crude product is recrystalized from EtOH (95 mL) to give the title compound as a white solid (8.13 g, 38.5 mmol). 1H NMR (CDCl3, 300 MHz) 3.73(t, 2H), 3.35(t, 2H), 2.20-2.08(m, 2H), 1.66(s, 6H). concentrated the crude product is recrystalized from EtOH (95 mL)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 5-methoxy-3,4-dihydro-2H-pyrrole (520 mg) in MeOH (8 mL) was added (1S)-1H-inden-1-amine, 2,3-dihydro (538 mg, 4.04 mmol, CAS 61341-86-4) at room temperature. The mixture was stirred at room temperature for 40 h. The reaction was then cooled to room temperature and concentrated. Flash column chromatography (5% 7N NH3 in MeOH/DCM) yielded (S)—N-(2,3-dihydro-1H-inden-1-yl)-3,4-dihydro-2H-pyrrol-5-amine, as a white solid. 1H NMR (300 MHz, CDCl3) δ: 7.30-7.39 (m, 5H), 7.13-7.28 (m, 3H), 5.25-5.38 (m, 1H), 3.72 (t, J=6.7 Hz, 2H), 2.91-3.04 (m, 1H), 2.77-2.91 (m, 1H), 2.54-2.72 (m, 1H), 2.35-2.54 (m, 2H), 1.93-2.10 (m, 2H), 1.76-1.91 (m, 1H). The reaction was then cooled to room temperature concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A slurry of 3.0 g (0.0152 mole) of powdered 2-phenylcyclopentylamine hydrochloride and 3 ml of O-methylbutyrolactim is allowed to stand at room temperature with occasional stirring for 6 days after which the material is covered with absolute ether. The solution is allowed to stand at room temperature for an additional 6 days. A precipitate forms which is collected and recrystallized from acetone-methanol and dried to give 2-[(2-phenylcyclopentyl)imino]pyrrolidine hydrochloride, M.P. 155°-158° C. to stand at room temperature to stand at room temperature for an additional 6 days A precipitate forms which is collected recrystallized from acetone-methanol dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 9.9 g (0.1 mole) of 2-methoxy-1-pyrroline and 24.4 g (0.15 mole) of 1-phenyl-1,3-butanedione are mixed together and, in a nitrogen atmosphere, heated with stirring for 18 hours in an oil bath at 100°. The dark reaction mixture is cooled to 60° and 500 ml of hexane is added. Upon further cooling to room temperature, the reaction product crystallises out. Recrystallisation from ethyl acetate/hexane yields 1-phenyl-2-(2-pyrrolidinylidene)-1,3-butanedione, m.p. 106°-108°. heated The dark reaction mixture is cooled to 60° the reaction product crystallises out Recrystallisation from ethyl acetate/hexane

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 9.9 g (0.1 mole) of 2-methoxy-1-pyrroline and 24.4 g (0.15 mole) of 1-phenyl-1,3-butanedione are mixed together and, in a nitrogen atmosphere, heated with stirring for 18 hours in an oil bath at 100°. The dark reaction mixture is cooled to 60° and 500 ml of hexane is added. Upon further cooling to room temperature, the reaction product crystallises out. Recrystallisation from ethyl acetate/hexane yields 1-phenyl-2-(2-pyrrolidinylidene)-1,3-butanedione, m.p. 106°-108°. heated The dark reaction mixture is cooled to 60° the reaction product crystallises out Recrystallisation from ethyl acetate/hexane