Isopropanol → Solifenacin

HRID 1171854Notes

Reaction equation

HRID 1171854 reaction equation
CC(O)C.[Na].[N:6]12[CH2:13][CH2:12][CH:9]([CH2:10][CH2:11]1)[C@@H:8]([OH:14])[CH2:7]2.CC([O:18][C:19]([N:21]1[CH2:30][CH2:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C@@H:22]1[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=O)C>CC(C)[O-].[Na+].CN(C=O)C.C1(C)C=CC=CC=1>[CH:34]1[CH:35]=[CH:36][C:31]([C@@H:22]2[N:21]([C:19]([O:14][C@@H:8]3[CH:9]4[CH2:12][CH2:13][N:6]([CH2:11][CH2:10]4)[CH2:7]3)=[O:18])[CH2:30][CH2:29][C:28]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]2=3)=[CH:32][CH:33]=1

Participants

8

Reactant 4

HCID 3776IsopropanolHCID 914043-Quinuclidinol, (-)-HCID 5360545SodiumHCID 67078773(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid propan-2-yl ester

Product 1

HCID 154059SolifenacinYield 64.7%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 109204432-Propanol, sodium salt (1:1)Solvent

Procedure

In a mixture of sodium isopropoxide prepared from 0.20 g of 2-propanol and 0.08 g of metallic sodium with 20 ml of toluene and 2.5 ml of DMF, 2.58 g of (R)-quinuclidin-3-ol was allowed to react with 5.00 g of (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid propan-2-yl ester for 8 hours while evaporating the solvent, thereby obtaining 3.97 g of a solifenacin-containing composition.

Workup

  1. customwhile evaporating the solvent

Sources & evidence

ORD record
ord-96d943b3aa024ce7998779cc47a6b581
Source dataset
uspto-grants-2010_11
Patent number
US07829715B2

Reaction notes

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