Ethyl chloroformate → Ethyl (1S)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

HRID 1620433Notes

Reaction equation

HRID 1620433 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([C@@H:7]2[N:16]([C:17]([O:19][C@@H:20]3C4CCN(CC4)[CH2:21]3)=[O:18])[CH2:15][CH2:14][C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]2=3)=[CH:5][CH:6]=1.C1([C@H]2C3C(=CC=CC=3)CCN2)C=CC=CC=1.ClC(OCC)=O>>[C:4]1([C@H:7]2[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH2:14][CH2:15][N:16]2[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1

Participants

4

Reactant 3

HCID 10928Ethyl chloroformateHCID 154059SolifenacinHCID 1382087(1S)-1,2,3,4-Tetrahydro-1-phenylisoquinoline

Product 1

HCID 25178885Ethyl (1S)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

Procedure

According to the process disclosed in U.S. Pat. No. 6,017,927, Solifenacin may be prepared by condensation of (1S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline of formula (III) with ethyl chloroformate to produce (1S)-ethyl 1-phenyl-1,2,3,4-tetrahydro-2-isoquinolinecarboxylate of formula (IV), which is further reacted with (R)-(−)-3-quinuclidinol of formula (V) to produce Solifenacin (II). Solifenacin is converted to Solifenacin hydrochloride by treating with HCl.

Sources & evidence

ORD record
ord-00c38d5e7d7b472cbc1825d2569ff17b
Source dataset
uspto-grants-2014_07
Patent number
US08772491B2

Reaction notes

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