methyl 1,2,3,5,6,7-hexahydropyrrolizine-8-carboxylate

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

Procedure: 8-(Methoxycarbonyl)-hexahydro-1H-pyrrolizine (from step 1d, 1.56 g, 9.22 mmol), acetone oxime (1.45 g, 19.8 mmol) and n-butyllithium (2.5M in hexane, 16 mL, 39.6 mmol) were combined in a similar fashion as that outlined by J. Saunders et at., J. Med. Chem. 1990, 33: 1128. The crude material was chromatographed (silica gel; CHCl3 /MeOH, 99:1) to afford a yellow oil (199 mg, 11%). MS (CI/NH3) m/e: 193 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ1.76-1.92 (m, 6H), 2.14-2.29 (m, 2H), 2.24 (s, 3H), 2.61-2.69 (m, 2H), 3.13-3.32 (m, 2H), 5.95 (s, 1H). The crude material was chromatographed (silica gel; CHCl3 /MeOH, 99:1)

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

Procedure: 8-(Methoxycarbonyl)-hexahydro-1H-pyrrolizine (from step 1d, 1.56 g, 9.22 mmol), acetone oxime (1.45 g, 19.8 mmol) and n-butyllithium (2.5M in hexane, 16 mL, 39.6 mmol) were combined in a similar fashion as that outlined by J. Saunders et at., J. Med. Chem. 1990, 33: 1128. The crude material was chromatographed (silica gel; CHCl3 /MeOH, 99:1) to afford a yellow oil (199 mg, 11%). MS (CI/NH3) m/e: 193 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ1.76-1.92 (m, 6H), 2.14-2.29 (m, 2H), 2.24 (s, 3H), 2.61-2.69 (m, 2H), 3.13-3.32 (m, 2H), 5.95 (s, 1H). The crude material was chromatographed (silica gel; CHCl3 /MeOH, 99:1)

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

Procedure: 8-(Methoxycarbonyl)-hexahydro-1H-pyrrolizine (from step 1d, 1.56 g, 9.22 mmol), acetone oxime (1.45 g, 19.8 mmol) and n-butyllithium (2.5M in hexane, 16 mL, 39.6 mmol) were combined in a similar fashion as that outlined by J. Saunders et at., J. Med. Chem. 1990, 33: 1128. The crude material was chromatographed (silica gel; CHCl3 /MeOH, 99:1) to afford a yellow oil (199 mg, 11%). MS (CI/NH3) m/e: 193 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ1.76-1.92 (m, 6H), 2.14-2.29 (m, 2H), 2.24 (s, 3H), 2.61-2.69 (m, 2H), 3.13-3.32 (m, 2H), 5.95 (s, 1H). The crude material was chromatographed (silica gel; CHCl3 /MeOH, 99:1)