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-methylpyrrolidin-1-yl]ethyl}-4-methyl-2-benzofuran-1(3H)-one

HRID 515119Notes

Reaction equation

HRID 515119 reaction equation
Cl.[NH2:2][CH2:3][C:4]1([CH3:23])[CH2:8][CH2:7][N:6]([CH2:9][C@@H:10]([C:12]2[CH:21]=[CH:20][C:15]3[C:16](=[O:19])[O:17][CH2:18][C:14]=3[C:13]=2[CH3:22])[OH:11])[CH2:5]1.[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:11][C@H:10]([C:12]1[CH:21]=[CH:20][C:15]2[C:16](=[O:19])[O:17][CH2:18][C:14]=2[C:13]=1[CH3:22])[CH2:9][N:6]1[CH2:7][CH2:8][C:4]([CH2:3][NH:2][CH2:37][C@H:35]([OH:36])[C:26]2[CH:27]=[CH:28][C:29]3[C:30](=[O:34])[O:31][CH2:32][C:33]=3[C:25]=2[CH3:24])([CH3:23])[CH2:5]1

Participants

3

Reactant 2

HCID 595686464-Methyl-5-((2R)-oxiran-2-yl)-2-benzofuran-1(3H)-one2×HCID 901905415-((1R)-2-(3-(aminomethyl)-3-methylpyrrolidin-1-yl)-1-hydroxyethyl)-4-methylisobenzofuran-1(3H)-one hydrochloride2×

Product 1

HCID 715657865-{(1R)-1-Hydroxy-2-[3-({[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]amino}methyl)-3-methylpyrrolidin-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-methylpyrrolidin-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-methylpyrrolidin-1-yl]-1-hydroxyethyl]-4-methyl-2-benzofuran-1(3H)-one hydrochloride [INTERMEDIATE 7] and 4-methyl-5-[(2R)-oxiran-2-yl]-2-benzofuran-1(3H)-one [INTERMEDIATE 2B].

Sources & evidence

ORD record
ord-16b8cd5a1adf4b929da3beec1b4d996b
Source dataset
uspto-grants-2015_08
Patent number
US09108947B2

Reaction notes

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