Ethanol → (-)-2-(1-hydroxy-1-(5-methoxy-7-methyl-1H-indol-4-yl)ethyl)benzo[d]oxazole-5-carbonitrile

HRID 2174081Notes

Reaction equation

HRID 2174081 reaction equation
C[O:2][C:3]([C:17]1[O:18][C:19]2[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][C:20]=2[N:21]=1)([C:5]1[C:13]([O:14][CH3:15])=[CH:12][C:11]([CH3:16])=[C:10]2[C:6]=1[CH:7]=[CH:8][NH:9]2)[CH3:4].CCO>C(=O)=O>[OH:2][C:3]([C:17]1[O:18][C:19]2[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][C:20]=2[N:21]=1)([C:5]1[C:13]([O:14][CH3:15])=[CH:12][C:11]([CH3:16])=[C:10]2[C:6]=1[CH:7]=[CH:8][NH:9]2)[CH3:4]

Participants

4

Reactant 2

HCID 702EthanolHCID 867017152-(1-methoxy-1-(5-methoxy-7-methyl-1H-indol-4-yl)ethyl)benzo[d]oxazole-5-carbonitrile

Product 1

HCID 86701713(-)-2-(1-hydroxy-1-(5-methoxy-7-methyl-1H-indol-4-yl)ethyl)benzo[d]oxazole-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 280Carbon DioxideSolvent

Procedure

Resolution of the enantiomers of 2-(1-methoxy-1-(5-methoxy-7-methyl-1H-indol-4-yl)ethyl)benzo[d]oxazole-5-carbonitrile was achieved by chiral SFC using a CHIRALPAK® AD-H column with 60% EtOH (0.2% DEA) in CO2 to give (+)-2-(1-hydroxy-1-(5-methoxy-7-methyl-1H-indol-4-yl)ethyl)benzo[d]oxazole-5-carbonitrile (tr=6.31 min) and (−)-2-(1-hydroxy-1-(5-methoxy-7-methyl-1H-indol-4-yl)ethyl)benzo[d]oxazole-5-carbonitrile (tr=11.01 min).

Sources & evidence

ORD record
ord-83a5d49b7406410e91ac5e8f5a9755ae
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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