8-benzyl-3-oxa-8-azabicyclo[3.2.1]octane-2,4-dione

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

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

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

Procedure: Benzylamine (25.7 g, 0.24 mol) was added to an ice cold solution of 8-benzyl-3-oxa-8-azabicyclo[3.2.1]octan-2,4-dione (0.24 mol; from step (a) above) in CH2Cl2 (1 L). The solution was stirred overnight at room temperature and concentrated in vacuo. The residue was dissolved in Et2O and extracted with 2 N NaOH solution. The aqueous base layer was separated and acidified to pH 4. The precipitated product was collected and dried to afford 49.5 g (61% for two steps) of the sub-title compound as a tan solid. concentrated in vacuo The residue was dissolved in Et2O extracted with 2 N NaOH solution The aqueous base layer was separated The precipitated product was collected dried

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

Procedure: A solution of cis-1-benzyl-2,5-pyrrolidinedicarboxylic acid (60 g, 0.24 mol; from Preparation A, step (c) above) and dicyclohexylcarbodiimide (49.7 g, 0.24 mol) in THF (1.2 L) was heated at reflux for 18 hours. The reaction was cooled and filtered to remove the urea by-product. The filtrate was concentrated in vacuo to afford a dark brown viscous oil which was used in the next step without further purification. at reflux for 18 hours The reaction was cooled filtered to remove the urea by-product The filtrate was concentrated in vacuo to afford a dark brown viscous oil which was used in the next step without further purification