HCID 69938195, compound → HCID 86674835, compound

HRID 1897579Notes

Reaction equation

HRID 1897579 reaction equation
[F:1][C:2]1[C:3]([CH:19]([OH:21])[CH3:20])=[C:4]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][C:11]=3[CH:12]=2)[CH:5]=[N:6][CH:7]=1>CCCCCCC>[F:1][C:2]1[C:3]([C@@H:19]([OH:21])[CH3:20])=[C:4]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][C:11]=3[CH:12]=2)[CH:5]=[N:6][CH:7]=1.[F:1][C:2]1[C:3]([C@H:19]([OH:21])[CH3:20])=[C:4]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][C:11]=3[CH:12]=2)[CH:5]=[N:6][CH:7]=1

Participants

4

Reactant 1

HCID 69938195HCID 69938195, compound

Product 2

HCID 86674835HCID 86674835, compoundHCID 86674836HCID 86674836, compound

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

The racemic mixture 7 (220 mg, 0.779 mmol) was separated by HPLC (ChiralPak AS-H, 21×250 mm, 90% heptane 10% ethanol, v/v) giving (S)-2-(5-fluoro-4-(1-hydroxyethyl)pyridin-3-yl)benzofuran-5-carbonitrile 7-(enantiomer-1) as white solid (72 mg) (retention time: 10.93 min) and (R)-2-(5-fluoro-4-(1-hydroxyethyl)pyridin-3-yl)benzofuran-5-carbonitrile 7-(enantiomer-2) as white solid (66 mg) (retention time: 12.57 min).

Sources & evidence

ORD record
ord-778d4e96e75146e98f324ec577b2f2b1
Source dataset
uspto-grants-2013_08
Patent number
US08519134B2

Reaction notes

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