HCID 58103588, compound → (R)-3-amino-3-(6-(trifluoromethyl)pyridin-3-yl)propan-1-ol

HRID 657745Notes

Reaction equation

HRID 657745 reaction equation
[NH2:1][CH:2]([C:6]1[CH:7]=[N:8][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:10][CH:11]=1)[CH2:3][CH2:4][OH:5]>CCCCCC.CCO>[NH2:1][C@H:2]([C:6]1[CH:7]=[N:8][C:9]([C:12]([F:15])([F:13])[F:14])=[CH:10][CH:11]=1)[CH2:3][CH2:4][OH:5].[NH2:1][C@@H:2]([C:6]1[CH:7]=[N:8][C:9]([C:12]([F:15])([F:13])[F:14])=[CH:10][CH:11]=1)[CH2:3][CH2:4][OH:5]

Participants

4

Reactant 1

HCID 58103588HCID 58103588, compound

Product 2

HCID 58103584(R)-3-amino-3-(6-(trifluoromethyl)pyridin-3-yl)propan-1-olHCID 58103598(s)-3-Amino-3-(6-(trifluoromethyl)pyridin-3-yl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 21879635Ethanol hexaneSolvent

Procedure

Racemic 3-amino-3-(6-(trifluoromethyl)pyridin-3-yl)propan-1-ol (1.10 g, 5.00 mmol) was resolved by chiral HPLC (conditions: CHIRALPAK AD-H column, 20×250 mm, hexane/EtOH [88:12] at 20 mL/min, UV at 230 nm) to yield (S)-3-amino-3-(6-(trifluoromethyl)pyridin-3-yl)propan-1-ol and (R)-3-amino-3-(6-(trifluoromethyl)pyridin-3-yl)propan-1-ol. Analytical chiral HPLC: CHIRALPAK AD-H column, 250×4.6 mm, hexane/EtOH [90:10] at 1.0 mL/min, UV at 230 nm); retention time for (S)-isomer: 18.68 min (>99% ee); retention time for (R)-isomer: 23.56 min (>99% ee).

Sources & evidence

ORD record
ord-c82db59c445a4fd889dd0b013999cf70
Source dataset
uspto-grants-2011_12
Patent number
US08076345B2

Reaction notes

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