4-Methyl-5-((2R)-oxiran-2-yl)-2-benzofuran-1(3H)-one → 5-{(1R)-1-Hydroxy-2-[2-({[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]amino}methyl)piperidin-1-yl]ethyl}-4-methyl-2-benzofuran-1(3H)-one
Reaction equation
Cl.[NH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][N:5]1[CH2:10][C@@H:11]([C:13]1[CH:22]=[CH:21][C:16]2[C:17](=[O:20])[O:18][CH2:19][C:15]=2[C:14]=1[CH3:23])[OH:12].[CH3:24][C:25]1[C:33]2[CH2:32][O:31][C:30](=[O:34])[C:29]=2[CH:28]=[CH:27][C:26]=1[C@@H:35]1[CH2:37][O:36]1>>[OH:12][C@H:11]([C:13]1[CH:22]=[CH:21][C:16]2[C:17](=[O:20])[O:18][CH2:19][C:15]=2[C:14]=1[CH3:23])[CH2:10][N:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH:4]1[CH2:3][NH:2][CH2:37][C@H:35]([OH:36])[C:26]1[CH:27]=[CH:28][C:29]2[C:30](=[O:34])[O:31][CH2:32][C:33]=2[C:25]=1[CH3:24]Participants
3
Reactant 2
Product 1
Procedure
5-{(1R)-1-Hydroxy-2-[2-({[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]amino}methyl)piperidin-1-yl]ethyl}-4-methyl-2-benzofuran-1(3H)-one was prepared in a similar fashion to that described for the synthesis of EXAMPLE 1 starting from 5-[(1R)-2-[2-(Aminomethyl)piperidin-1-yl]-1-hydroxyethyl}-4-methyl-2-benzofuran-1(3H)-one hydrochloride [INTERMEDIATE 6] and 4-methyl-5-[(2R)-oxiran-2-yl]-2-benzofuran-1(3H)-one [INTERMEDIATE 2B].
Sources & evidence
- ORD record
- ord-7779d447e2d646298507822b2a50e9bd
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09108947B2
Reaction notes
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