Potassium Carbonate → 4-[3-(4-Trifluoromethoxy-phenyl)-3,9-diaza-bicyclo[3.3.1]nonane-9-sulfonyl]-indan-2-carboxylic acid methyl ester
Reaction equation
COC(C1CC2C(=CC=CC=2)C1)=O.[F:14][C:15]([F:33])([F:32])[O:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:30][CH:29]3[NH:31][CH:25]([CH2:26][CH2:27][CH2:28]3)[CH2:24]2)=[CH:19][CH:18]=1.[CH3:34][O:35][C:36]([CH:38]1[CH2:46][C:45]2[C:40](=[CH:41][CH:42]=[CH:43][C:44]=2[S:47](Cl)(=[O:49])=[O:48])[CH2:39]1)=[O:37].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:34][O:35][C:36]([CH:38]1[CH2:46][C:45]2[C:40](=[CH:41][CH:42]=[CH:43][C:44]=2[S:47]([N:31]2[CH:29]3[CH2:28][CH2:27][CH2:26][CH:25]2[CH2:24][N:23]([C:20]2[CH:21]=[CH:22][C:17]([O:16][C:15]([F:14])([F:32])[F:33])=[CH:18][CH:19]=2)[CH2:30]3)(=[O:49])=[O:48])[CH2:39]1)=[O:37]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
4-|3-(4-trifluoromethoxy-phenyl)-3,9-diaza-bicyclo|3.3.1|nonane-9-sulfonyl|-indan-2-carboxylic acid methyl ester: A mixture of 3-(4-trifluoromethoxy-phenyl)-3,9-diaza-bicyclo[3.3.1]nonane (60 mg, 0.21 mmol), 4-chlorosulfonyl-indan-2(R,S)-carboxylic acid methyl ester (120 mg, 0.44 mmol), potassium carbonate (200 mg, 1.4 mmol), and acetonitrile (3 mL) were heated at 50° C. for 2 h. The mixture was filtered through Celite, concentrated, and purified by silica gel chromatography (9:1→4:1; hexanes:ethyl acetate) to give 4-[3-(4-trifluoromethoxy-phenyl)-3,9-diaza-bicyclo[3.3.1]nonane-9-sulfonyl]-indan-2-carboxylic acid methyl ester: MS (ESI): 525.5 (M+H).
Workup
- filtrationThe mixture was filtered through Celite
- concentrationconcentrated
- custompurified by silica gel chromatography (9:1→4:1; hexanes:ethyl acetate)
Sources & evidence
- ORD record
- ord-29931949e8784295a9a0cfffcb914be1
- Source dataset
- uspto-grants-2009_04
- Patent number
- US07517884B2
Reaction notes
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