Acetic Acid → 3-{[4-(BOC-methyl-amino)-cyclohexylamino]-methyl}-4-fluoro-benzene boronic acid
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([B:8]([OH:10])[OH:9])=[CH:4][C:3]=1[CH:11]=O.[C:13]([O:17][C:18](=[O:27])[NH:19][C@H:20]1[CH2:25][CH2:24][C@H:23]([NH2:26])[CH2:22][CH2:21]1)([CH3:16])([CH3:15])[CH3:14].[CH3:28]C(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>C1COCC1.C1(C)C=CC=CC=1.CCOC(C)=O>[C:18]([N:19]([CH3:28])[CH:20]1[CH2:21][CH2:22][CH:23]([NH:26][CH2:11][C:3]2[CH:4]=[C:5]([B:8]([OH:9])[OH:10])[CH:6]=[CH:7][C:2]=2[F:1])[CH2:24][CH2:25]1)([O:17][C:13]([CH3:16])([CH3:14])[CH3:15])=[O:27]Participants
9
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Procedure
To a solution of 4-fluoro-3-formyl benzene boronic acid (0.88 g, 5.99 mmol) in THF (5 mL) and toluene (5 mL) was added amine (3) (1.4 g, 7.19 mmol) followed by AcOH (0.34 mL, 7.19 mmol), and the resulting solution was stirred at RT for 18 h. After this time sodium triacetoxyborohydride (1.57 g, 8.38 mmol) was added and the resulting solution was stirred at RT for a further 6 h. EtOAc (10 mL) was added to the reaction mixture followed by dropwise addition of sat. NaHCO3 solution (10 mL). The organic layer was separated and the aqueous layer was extracted into EtOAc (2×10 mL). The combined organic layers were dried (MgSO4), filtered and reduced in vacuo to give the title compound as a yellow solid.
Workup
- stirringthe resulting solution was stirred at RT for a further 6 h
- customThe organic layer was separated
- extractionthe aqueous layer was extracted into EtOAc (2×10 mL)
- dry with materialThe combined organic layers were dried (MgSO4)
- filtrationfiltered
Sources & evidence
- ORD record
- ord-3a690ab6a6194cac91a268347ed6e438
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08273747B2
Reaction notes
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