Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH:14]2[CH:10]([CH2:11][C:12]([C:16]([O:18]C)=[O:17])=[CH:13]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>C1COCC1.CO>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]2[CH:14]([CH2:13][C:12]([C:16]([OH:18])=[O:17])=[CH:11]2)[CH2:15]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
Procedure
To a solution of methyl 3-(tert-butoxycarbonyl)-3-azabicyclo[3.3.0]-oct-6-ene-7-carboxylate (0.350 g, 1.31 mmol) in THF-methanol (6.0 mL, 1:1) was added a solution of lithium hydroxide (0.100 g in 1 mL of water, 3.94 mmol), and the reaction was stirred at ambient temperature for 3 h. The solvent was evaporated, the residue was acidified to pH 4 with 1 M aqueous hydrochloric acid, and extracted with ethyl acetate (50 mL). The organic layer was washed with water (50 mL) and brine (50 mL), dried (anhydrous sodium sulfate), and concentrated to obtain 0.31 g (92% yield) of 3-(tert-butoxycarbonyl)-3-azabicyclo[3.3.0]-oct-6-ene-7-carboxylic acid, as a white solid (1H NMR (CDCl3, 300 MHz): δ 6.76 (bs, 1H), 3.76-3.62 (m, 1H), 3.58-3.42 (m, 2H), 3.11-2.94 (m, 2H), 2.84-2.67 (m, 1H), 2.46-2.23 (m, 1H), 1.42 (s, 9H). MS (m/z): 254 (M+1), 198 (M+1-56)).
Workup
- customThe solvent was evaporated
- extractionextracted with ethyl acetate (50 mL)
- washThe organic layer was washed with water (50 mL) and brine (50 mL)
- dry with materialdried (anhydrous sodium sulfate)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-4911542411dc4b39862ba0f96a5cd79e
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08198296B2
Linked notes
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