1-(4-(Trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline → (R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

HRID 445273

Reaction equation

HRID 445273 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][NH:10]2)=[CH:5][CH:4]=1.CO.C(=O)=O>>[F:20][C:2]([F:1])([F:19])[C:3]1[CH:4]=[CH:5][C:6]([C@@H:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][NH:10]2)=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 166406961-(4-(Trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinolineHCID 21973728Carbon dioxide methanol

Product 1

HCID 28293305(R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

Procedure

Enantiomers of 1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (2.120 g, 7.46 mmol, racemic mixture) were separated using chiral SFC (Chiralcel AD-H (250×21 Mm), 45% methanol/CO2 (100 bar), 65 mL/min, 220 nm) to give the title compound as a light yellow solid. MS (ESI, positive ion) m/z: 278 (M+H).

Sources & evidence

ORD record
ord-eb1ae6770acf47df85bdc8dca904749e
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Linked notes

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