Ethyl 3-isocyanatobenzoate → Ethyl 3-(2-benzyl-2-azabicyclo[2.2.1]hept-7-ylmethoxycarbonylamino)benzoate
Reaction equation
[CH2:1]([N:8]1[CH2:13][CH:12]2[CH:14]([CH2:15][OH:16])[CH:9]1[CH2:10][CH2:11]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:17]([C:20]1[CH:21]=[C:22]([CH:28]=[CH:29][CH:30]=1)[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:18]=[O:19]>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH:12]2[CH:14]([CH2:15][O:16][C:18]([NH:17][C:20]3[CH:21]=[C:22]([CH:28]=[CH:29][CH:30]=3)[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:19])[CH:9]1[CH2:10][CH2:11]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
Procedure
200.00 mg (0.920 mmol) of (2-benzyl-2-aza-bicyclo[2.2.1]hept-7yl)methanol were dissolved in 3 ml of dry THF and then 176.00 mg (0.920 mmol) of ethyl 3-isocyanatobenzoate in 1 ml of dry THF were added at room temperature. After stirring for 6 hours at room temperature, 125 mg (0.30 mmol) of tris-(2-aminoethyl)amine-polystyrene and 250 mg (0.30 mmol) of methyl isocyanate-polystyrene (each from NovaBiochem) were added and stirred at 50° C. overnight. After the resins had been filtered off, the solvent was removed and the required product was purified by chromatography with ethyl acetate as mobile phase. In this way, 220.00 mg (0.539 mmol) of ethyl 3-(2-benzyl-2-azabicyclo[2.2.1]hept-7-ylmethoxycarbonylamino)benzoate were obtained in the form of a colorless solid.
Workup
- stirringstirred at 50° C. overnight
- filtrationAfter the resins had been filtered off
- customthe solvent was removed
- customthe required product was purified by chromatography with ethyl acetate as mobile phase
Sources & evidence
- ORD record
- ord-b62b452f58ed43caaf6d5b27fede0eb1
- Source dataset
- uspto-grants-2006_03
- Patent number
- US07008955B2
Reaction notes
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