Ethanol → (2R)-(-)-3-[4-(6-chloro-3-indolyl)-1,2,3,6-tetrahydropyridin-1-yl]-1-(5-quinolinyloxy)-2-propanol

HRID 565525Notes

Reaction equation

HRID 565525 reaction equation
[O:1]1[CH2:3][C@@H:2]1[CH2:4][O:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][CH:10]=[N:11]2.[Cl:16][C:17]1[CH:25]=[C:24]2[C:20]([CH:21]=[C:22](C3CCNCC=3)[NH:23]2)=[CH:19][CH:18]=1.[CH2:32](O)[CH3:33]>CS(C)=O>[Cl:16][C:17]1[CH:25]=[C:24]2[C:20]([C:21]([C:8]3[CH2:9][CH2:10][N:11]([CH2:3][C@@H:2]([OH:1])[CH2:4][O:5][C:6]4[CH:15]=[CH:14][CH:13]=[C:12]5[C:7]=4[CH:8]=[CH:9][CH:10]=[N:11]5)[CH2:32][CH:33]=3)=[CH:22][NH:23]2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 11735808(R)-5-(Oxiran-2-ylmethoxy)quinolineHCID 212683476-chloro-2-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

Product 1

HCID 53815837(2R)-(-)-3-[4-(6-chloro-3-indolyl)-1,2,3,6-tetrahydropyridin-1-yl]-1-(5-quinolinyloxy)-2-propanol

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The title compound was prepared in a fashion similar to that described in Example 1 using (R)-5-(oxiranylmethoxy)-quinoline (0.495 g, 2.46 mmol) and 6-chloro-2-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole (0.519 g, 2.33 mmol) using ethanol as reaction solvent. Yield 0.840 g (87%) of a tan powder. FDMS m/e=433 (M+ of free base). mp 221-223° C. α[D]589=−9.9 (c=1.00, dimethylsulfoxide).

Workup

  1. customas reaction solvent

Sources & evidence

ORD record
ord-4a51288adbfe453c9bb7806b940f6599
Source dataset
uspto-grants-2001_01
Patent number
US06172073B2

Reaction notes

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