(R)-6-(2-(9-((R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)-3-oxa-7,9-diazabicyclo[3.3.1]nonan-7-yl)ethyl)-3-methylisochroman-1-one → (S)-6-(2-(9-((R)-2-Hydroxy-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)-3-oxa-7,9-diazabicyclo[3.3.1]nonan-7-yl)ethyl)-3-methylisochroman-1-one

HRID 2281347Notes

Reaction equation

HRID 2281347 reaction equation
[OH:1][C@H:2]([C:27]1[C:28]([CH3:37])=[C:29]2[C:33](=[CH:34][CH:35]=1)[C:32](=[O:36])[O:31][CH2:30]2)[CH2:3][N:4]1[CH:9]2[CH2:10][N:11]([CH2:13][CH2:14][C:15]3[CH:16]=[C:17]4[C:22](=[CH:23][CH:24]=3)[C:21](=[O:25])[O:20][C@H:19]([CH3:26])[CH2:18]4)[CH2:12][CH:5]1[CH2:6][O:7][CH2:8]2.O[C@H](C1C=CC2C(=O)OCC=2C=1C)CN1C2CNCC1COC2.C[C@H]1CC2C(=CC=C(CC=O)C=2)C(=O)O1>>[OH:1][C@H:2]([C:27]1[C:28]([CH3:37])=[C:29]2[C:33](=[CH:34][CH:35]=1)[C:32](=[O:36])[O:31][CH2:30]2)[CH2:3][N:4]1[CH:5]2[CH2:12][N:11]([CH2:13][CH2:14][C:15]3[CH:16]=[C:17]4[C:22](=[CH:23][CH:24]=3)[C:21](=[O:25])[O:20][C@@H:19]([CH3:26])[CH2:18]4)[CH2:10][CH:9]1[CH2:8][O:7][CH2:6]2

Participants

4

Reactant 3

HCID 71557350(R)-6-(2-(9-((R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)-3-oxa-7,9-diazabicyclo[3.3.1]nonan-7-yl)ethyl)-3-methylisochroman-1-oneHCID 89543621(S)-2-(3-Methyl-1-oxoisochroman-6-yl)acetaldehyde2×HCID 1176420375-[(1R)-1-Hydroxy-2-(3-oxa-7,9-diazabicyclo[3.3.1]non-9-yl)ethyl]-4-methyl-2-benzofuran-1-(3H)-one2×

Product 1

HCID 71557351(S)-6-(2-(9-((R)-2-Hydroxy-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)-3-oxa-7,9-diazabicyclo[3.3.1]nonan-7-yl)ethyl)-3-methylisochroman-1-one

Procedure

(S)-6-(2-(9-((R)-2-Hydroxy-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)-3-oxa-7,9-diazabicyclo[3.3.1]nonan-7-yl)ethyl)-3-methylisochroman-1-one was prepared in an analogous fashion to that described for the synthesis of (R)-6-(2-(9-((R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)-3-oxa-7,9-diazabicyclo[3.3.1]nonan-7-yl)ethyl)-3-methylisochroman-1-one (EXAMPLE 21) starting from 5-[(1R)-1-hydroxy-2-(3-oxa-7,9-diazabicyclo[3.3.1]non-9-yl)ethyl]-4-methyl-2-benzofuran-1 (3H)-one (INTERMEDIATE 17) and (S)-2-(3-Methyl-1-oxoisochroman-6-yl)acetaldehyde (INTERMEDIATE 22).

Sources & evidence

ORD record
ord-9dc916b4ddec4ec4995c3b3ba8c21b87
Source dataset
uspto-grants-2015_09
Patent number
US09139585B2

Reaction notes

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