(S)-alpha-(2'-(2-Hydroxy-3-(4-(naphthalen-2-yl)piperidino)propyloxy)benzylidene)-gamma-butyrolactone → (Z)-(S)-alpha-(2'-(2-hydroxy-3-(4-(naphthalen-2-yl)piperidino)-propyloxy)benzylidene)-gamma-butyrolactone

HRID 460668Notes

Reaction equation

HRID 460668 reaction equation
[OH:1][C@@H:2]([CH2:18][N:19]1[CH2:24][CH2:23][CH:22]([C:25]2[CH:34]=[CH:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=2)[CH2:21][CH2:20]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(O)C>[OH:1][C@@H:2]([CH2:18][N:19]1[CH2:20][CH2:21][CH:22]([C:25]2[CH:34]=[CH:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=2)[CH2:23][CH2:24]1)[CH2:3][O:4][C:5]1[CH:17]=[CH:16][CH:15]=[CH:14][C:6]=1/[CH:7]=[C:8]1\[C:9]([O:11][CH2:12][CH2:13]\1)=[O:10]

Participants

3

Reactant 1

HCID 69497913(S)-alpha-(2'-(2-Hydroxy-3-(4-(naphthalen-2-yl)piperidino)propyloxy)benzylidene)-gamma-butyrolactone

Product 1

HCID 9868720(Z)-(S)-alpha-(2'-(2-hydroxy-3-(4-(naphthalen-2-yl)piperidino)-propyloxy)benzylidene)-gamma-butyrolactoneYield 15%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(S)-α-(2′-(2-Hydroxy-3-(4-(naphthalen-2-yl)piperidino)propyloxy)benzylidene)-γ-butyrolactone (2.0 g) was dissolved in ethanol (300 ml) and exposed to the sunlight for 6 hr. The solvent was concentrated under reduced pressure and the obtained oil was purified by silica gel column chromatography (chloroform/methanol) to give the title compound (0.3 g).

Workup

  1. concentrationThe solvent was concentrated under reduced pressure
  2. customthe obtained oil was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-74bb04fbab7c44df8362c41849e711b3
Source dataset
uspto-grants-2007_03
Patent number
US07196199B2

Reaction notes

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