(1S)-1,2,3,4-Tetrahydro-1-phenylisoquinoline → Solifenacin

HRID 2061897Notes

Reaction equation

HRID 2061897 reaction equation
[C:1](=[O:21])(OC1C=CC([N+]([O-])=O)=CC=1)[O:2][C@@H:3]1[CH:8]2[CH2:9][CH2:10][N:5]([CH2:6][CH2:7]2)[CH2:4]1.[C:22]1([C@H:28]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH2:31][CH2:30][NH:29]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[N:5]12[CH2:6][CH2:7][CH:8]([CH2:9][CH2:10]1)[C@@H:3]([O:2][C:1]([N:29]1[CH2:30][CH2:31][C:32]3[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=3)[C@@H:28]1[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:21])[CH2:4]2

Participants

3

Reactant 2

HCID 1382087(1S)-1,2,3,4-Tetrahydro-1-phenylisoquinolineHCID 46913243HCID 46913243, compound

Product 1

HCID 154059Solifenacin

Procedure

The above mentioned step (b) comprises treating the reaction mixture comprising (3R)-1-azabicyclo[2.2.2]oct-3-yl 4-nitrophenyl carbonate of formula (IV) of step (a) with (1S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline of formula (V) in an organic solvent and in an inert atmosphere at temperature of −20 to 50° C. to obtain (1S)-(3R)-1-azabicyclo[2.2.2]oct-3-yl-3,4-dihydro-1-phenyl-2(1H)-isoquinolinecarboxylate (Solifenacin) of formula (I).

Sources & evidence

ORD record
ord-3a9971d2ca8141a2b924c31fce03c091
Source dataset
uspto-grants-2012_10
Patent number
US08283470B2

Reaction notes

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