Methane → 1-amino-4-[(1S)(4S)-2-benzyl-2,5-diazabicyclo{2.2.1}heptan-5-yl]-3-fluorobenzene

Participants

Reaction Conditions

Reaction Steps

Hydrazine hydrate (0.57 ml) was added to a suspension of 4-[(1S)(4S)-2-benzyl-2,5-diazabicyclo{2,2,1}heptan-5-yl]-3-fluoro-1-nitrobenzene (1.63 g, 5 mmol) in ethanol (35 ml) with stirring, followed by Raney nickel (˜1 g). The mixture was heated at 60° C. for 1.5 hours. More hydrazine hydrate (0.2 ml) and Raney nickel (˜0.5 g) were added and heating continued for a further 3 hours. The mixture was cooled and stirred with charcoal (0.5 g) for 1 hour and filtered. The filtrate was evaporated to give 1-amino-4-[(1S)(4S)-2-benzyl-2,5-diazabicyclo{2.2.1}heptan-5-yl]-3-fluorobenzene (1.28 g, 86%) as an oil. MS: 287 (MH+); NMR(CDCl3); 1.8-1.95 (2H, dd); 2.73-2.9 (2H, dd); 3.17-3.5 (5H, m); 3.71 (2H, s); 4.12 (1H, s); 6.32-6.52 (3H, m); 7.18-7.35 (5H+CHCl3).

Provenance & Evidence