Boron trifluoride → 3-Benzyl-6-nitro-3-azabicyclo[3.1.0]hexane

To a solution of 3-benzyl-6-nitro-3-azabicyclo[3.1.0]hexane-2,4-dione (3.0 g, 12.2 mmol) in dry THF (30 ml) was added NaBH4 (1.15 g, 30.48 mmol). The reaction was stirred for 15 min at r.t. under N2. BF3.THF complex (3.15 ml, 13.4 mmol) was added dropwise and the reaction heated at 40° C. for 4 h. Further NaBH4 (0.15 g) was added followed by BF3.THF complex (0.32 ml). Heating was continued at 45° C. for 30 min. A mixture of THF/H2O (1/1, 60 ml) was added dropwise with stirring. The resulting mixture was heated at 50° C. for 1 h before standing at r.t. for 16 h. The THF was removed to leave mainly water. This was extracted with EtOAc, dried (MgSO4) and evaporated to dryness to give the title compound as a yellow oil (2.47 g, 93%). m/z 219 [M+H]+, 1H NMR (300 MHz, CDCl3) δ: 2.50 (4H, s), 3.15 (2H, d), 3.65 (1H, s), 4.55 (1H, s), 7.2-7.4 (5H, m).

1. additionTHF complex (3.15 ml, 13.4 mmol) was added dropwise
2. temperaturethe reaction heated at 40° C. for 4 h
3. temperatureHeating
4. waitwas continued at 45° C. for 30 min
5. additionwas added dropwise
6. stirringwith stirring
7. temperatureThe resulting mixture was heated at 50° C. for 1 h
8. waitbefore standing at r.t. for 16 h
9. customThe THF was removed
10. customto leave mainly water
11. extractionThis was extracted with EtOAc
12. dry with materialdried (MgSO4)
13. customevaporated to dryness

ORD record

ord-c65e5446fa1c492aa010bade7a3b7eaa

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07932246B2