4-Methyl-5-((2R)-oxiran-2-yl)-2-benzofuran-1(3H)-one → 5-{(1R)-1-Hydroxy-2-[3-({[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]amino}methyl)-3-methylpiperidin-1-yl]ethyl}-4-methyl-2-benzofuran-1(3H)-one

HRID 515120Notes

Reaction equation

HRID 515120 reaction equation
Cl.[NH2:2][CH2:3][C:4]1([CH3:24])[CH2:9][CH2:8][CH2:7][N:6]([CH2:10][C@@H:11]([C:13]2[CH:22]=[CH:21][C:16]3[C:17](=[O:20])[O:18][CH2:19][C:15]=3[C:14]=2[CH3:23])[OH:12])[CH2:5]1.[CH3:25][C:26]1[C:34]2[CH2:33][O:32][C:31](=[O:35])[C:30]=2[CH:29]=[CH:28][C:27]=1[C@@H:36]1[CH2:38][O:37]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:6]1[CH2:7][CH2:8][CH2:9][C:4]([CH2:3][NH:2][CH2:38][C@H:36]([OH:37])[C:27]2[CH:28]=[CH:29][C:30]3[C:31](=[O:35])[O:32][CH2:33][C:34]=3[C:26]=2[CH3:25])([CH3:24])[CH2:5]1

Participants

3

Reactant 2

HCID 595686464-Methyl-5-((2R)-oxiran-2-yl)-2-benzofuran-1(3H)-one2×HCID 904099395-((1R)-2-(3-(aminomethyl)-3-methylpiperidin-1-yl)-1-hydroxyethyl)-4-methylisobenzofuran-1(3H)-one hydrochloride2×

Product 1

HCID 715657875-{(1R)-1-Hydroxy-2-[3-({[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]amino}methyl)-3-methylpiperidin-1-yl]ethyl}-4-methyl-2-benzofuran-1(3H)-one

Procedure

5-{(1R)-1-Hydroxy-2-[3-({[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]amino}methyl)-3-methylpiperidin-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-[(R)-2-[3-(aminomethyl)-3-methylpiperidin-1-yl]-1-hydroxyethyl]-4-methyl-2-benzofuran1(3H)-one hydrochloride [INTERMEDIATE 8] and 4-methyl-5-[(2R)-oxiran-2-yl]-2-benzofuran-1 (3H)-one [INTERMEDIATE 2B].

Sources & evidence

ORD record
ord-55fdc737fe6e4ea190816f81821b2994
Source dataset
uspto-grants-2015_08
Patent number
US09108947B2

Reaction notes

Loading…