(1S,2S)-2-aminocyclohexanol → HCID 56643780, compound

HRID 2365254Notes

Reaction equation

HRID 2365254 reaction equation
O[C@H]1CCCC[C@@H]1[N:8]1[CH2:16][C:15]2[C:14]3[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=3[C:12]([CH2:21][C:22]3[CH:23]=[N:24][C:25](SC)=[CH:26][CH:27]=3)=[CH:11][C:10]=2[C:9]1=[O:30].N[C@H]1CCCC[C@@H:33]1[OH:38].ClCC1C=CC(SC)=NC=1>>[CH3:33][O:38][C:25]1[N:24]=[CH:23][C:22]([CH2:21][C:12]2[C:13]3[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=3[C:15]3[CH2:16][NH:8][C:9](=[O:30])[C:10]=3[CH:11]=2)=[CH:27][CH:26]=1

Participants

4

Reactant 3

HCID 7057408(1S,2S)-2-aminocyclohexanolHCID 13752889HCID 13752889, compoundHCID 68622221HCID 68622221, compound

Product 1

HCID 56643780HCID 56643780, compound

Procedure

5-[(6-Methoxypyridin-3-yl)methyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one was prepared employing the procedures described for the construction of 2-[(1S,2S)-2-hydroxycyclohexyl]-5-{[6-(methylthio)pyridine-3-yl]methyl}-1,2-dihydro-3H-benzo[e]isoindol-3-one in Example 10, substituting ammonium hydroxide for (1S,2S)-2-aminocyclohexanol, and substituting 5-(chloromethyl)-2-methoxypyridine for 5-(chloromethyl)-2-(methylthio)pyridine.

Sources & evidence

ORD record
ord-a884ee47dcc84baea5bdc282e29da433
Source dataset
uspto-grants-2014_04
Patent number
US08697690B2

Reaction notes

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