4-(Naphthalen-1-YL)piperidine → (S)-alpha-(2'-(2-hydroxy-3-(4-(naphthalen-1-yl)piperidino)-propyloxy) benzylidene)-gamma-butyrolactone p-toluenesulfonate

HRID 460661Notes

Reaction equation

HRID 460661 reaction equation
[O:1]1[CH2:18][C@H:2]1[CH2:3][O:4][C:5]1[CH:17]=[CH:16][CH:15]=[CH:14][C:6]=1[CH:7]=[C:8]1[CH2:13][CH2:12][O:11][C:9]1=[O:10].[C:19]1([CH:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1.C(OCC)(=O)C.[C:41]1([CH3:51])[CH:46]=[CH:45][C:44]([S:47]([OH:50])(=[O:49])=[O:48])=[CH:43][CH:42]=1>CO>[C:41]1([CH3:51])[CH:42]=[CH:43][C:44]([S:47]([OH:50])(=[O:48])=[O:49])=[CH:45][CH:46]=1.[OH:1][C@@H:2]([CH2:18][N:32]1[CH2:33][CH2:34][CH:29]([C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=[CH:21][CH:20]=2)[CH2:30][CH2:31]1)[CH2:3][O:4][C:5]1[CH:17]=[CH:16][CH:15]=[CH:14][C:6]=1[CH:7]=[C:8]1[CH2:13][CH2:12][O:11][C:9]1=[O:10]

Participants

5

Reactant 3

HCID 148193164-(Naphthalen-1-YL)piperidineHCID 22729081Ethyl acetate p-toluenesulfonic acidHCID 86585643(S)-alpha-(2'-(2,3-epoxypropan-1-yloxy)benzylidene)-gamma-butyrolactone

Product 1

HCID 86585644(S)-alpha-(2'-(2-hydroxy-3-(4-(naphthalen-1-yl)piperidino)-propyloxy) benzylidene)-gamma-butyrolactone p-toluenesulfonate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The reaction was performed in same manner as in Example 307 using (S)-α-(2′-(2,3-epoxypropan-1-yloxy)benzylidene)-γ-butyrolactone (5.8 g) and 4-(naphthalen-1-yl)piperidine (5.0 g) in methanol (100 ml) and the obtained oil was treated with ethyl acetate/p-toluenesulfonic acid to give the title compound (7.8 g), melting point 119–121° C.

Sources & evidence

ORD record
ord-478416083fa84ddbbca7f8dd59ab4388
Source dataset
uspto-grants-2007_03
Patent number
US07196199B2

Reaction notes

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