(2S)-alpha-(2'-(2,3-Epoxypropan-1-yloxy)benzyl)-gamma-butyrolactone → (2S)-alpha-(2'-(2-hydroxy-3-(4-(naphthalen-2-yl)piperidino)propyloxy)benzyl)-gamma-butyrolactone

HRID 460671Notes

Reaction equation

HRID 460671 reaction equation
[O:1]1[CH2:18][CH:2]1[CH2:3][O:4][C:5]1[CH:17]=[CH:16][CH:15]=[CH:14][C:6]=1[CH2:7][C@H:8]1[CH2:13][CH2:12][O:11][C:9]1=[O:10].[CH:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][C:20]=1[CH:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1>CO>[OH:1][CH:2]([CH2:18][N:32]1[CH2:33][CH2:34][CH:29]([C:20]2[CH:21]=[CH:22][C:23]3[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:19]=2)[CH2:30][CH2:31]1)[CH2:3][O:4][C:5]1[CH:17]=[CH:16][CH:15]=[CH:14][C:6]=1[CH2:7][C@H:8]1[CH2:13][CH2:12][O:11][C:9]1=[O:10]

Participants

4

Reactant 2

HCID 21306424(2S)-alpha-(2'-(2,3-Epoxypropan-1-yloxy)benzyl)-gamma-butyrolactoneHCID 220292644-(Naphthalen-2-yl)piperidine

Product 1

HCID 18446010(2S)-alpha-(2'-(2-hydroxy-3-(4-(naphthalen-2-yl)piperidino)propyloxy)benzyl)-gamma-butyrolactoneYield 46.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(2S)-α-(2′-(2,3-Epoxypropan-1-yloxy)benzyl)-γ-butyrolactone (1.5 g) and 4-(naphthalen-2-yl)piperidine (1.5 g) were dissolved in methanol (50 ml) and the reaction mixture was refluxed under heating for 2 hr. After cooling, the solvent was evaporated under reduced pressure and the obtained oil was purified by silica gel column chromatography (chloroform/methanol) to give the title compound (1.3 g).

Workup

  1. temperaturethe reaction mixture was refluxed
  2. temperatureunder heating for 2 hr
  3. temperatureAfter cooling
  4. customthe solvent was evaporated under reduced pressure
  5. customthe obtained oil was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-84e0bb8b1b2b43f5a6bad88475034da6
Source dataset
uspto-grants-2007_03
Patent number
US07196199B2

Reaction notes

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