1-[(Tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid → 3-{5-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1H-imidazol-2-yl}-2-azabicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]1[NH:14][C:15]([C:18]2[CH:23]=[CH:22][C:21]([B:24]3[O:28][C:27]([CH3:30])([CH3:29])[C:26]([CH3:32])([CH3:31])[O:25]3)=[CH:20][CH:19]=2)=[CH:16][N:17]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:33](OC(N1CCCC1C(O)=O)=O)(C)(C)[CH3:34]>>[C:1]([O:5][C:6]([N:8]1[CH:9]([C:13]2[NH:14][C:15]([C:18]3[CH:23]=[CH:22][C:21]([B:24]4[O:25][C:26]([CH3:32])([CH3:31])[C:27]([CH3:30])([CH3:29])[O:28]4)=[CH:20][CH:19]=3)=[CH:16][N:17]=2)[CH:10]2[CH2:11][CH:12]1[CH2:33][CH2:34]2)=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
3
Reactant 2
Product 1
Procedure
3-{5-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1H-imidazol-2-yl}-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester was prepared following the procedure for 2-{5-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1H-imidazol-2-yl}-pyrrolidine-1-carboxylic acid tert-butyl ester, substituting 2-Aza-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid 2-tert-butyl ester for Pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester. LCMS-ESI+: calc'd for C26H36BN3O4: 465.28 (M+); Found: 466.21 (M+H+).
Sources & evidence
- ORD record
- ord-f1f7a6bd13cb4ecd8d2e552a61d764ab
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09156823B2
Reaction notes
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