1-t-Butoxycarbonyl-4-(2-{2-[2-(3-methoxymethoxyphenyl)ethyl]phenoxy}ethyl)piperidine → 4-(2-{2-[2-(3-Methoxymethoxyphenyl)ethyl]phenoxy}ethyl)-1-methylpiperidine

HRID 743279Notes

Reaction equation

HRID 743279 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH2:32][O:33][CH3:34])[CH:26]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:34][O:33][CH2:32][O:31][C:27]1[CH:26]=[C:25]([CH2:24][CH2:23][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[O:16][CH2:15][CH2:14][CH:11]2[CH2:10][CH2:9][N:8]([CH3:6])[CH2:13][CH2:12]2)[CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 194238641-t-Butoxycarbonyl-4-(2-{2-[2-(3-methoxymethoxyphenyl)ethyl]phenoxy}ethyl)piperidineHCID 21226445Aluminium lithium hydride

Product 1

HCID 194240154-(2-{2-[2-(3-Methoxymethoxyphenyl)ethyl]phenoxy}ethyl)-1-methylpiperidineYield 62.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following a procedure similar to that described in Example 38, 1.40 g of 1-t-butoxycarbonyl-4-(2-{2-[2-(3-methoxymethoxyphenyl) ethyl]phenoxy }ethyl) piperidine [prepared as described in Example 55 (a) ] were reacted with 240 mg of lithium aluminum hydride dispersed in 30 ml of tetrahydrofuran. The mixture was then worked up as described in Example 38, and the crude product thus obtained was purified by column chromatography through silica gel, using a 10:1 by volume mixture of methylene chloride and methanol as the eluent, to give 710 mg of the title compound as a colorless oil.

Workup

  1. customthe crude product thus obtained
  2. customwas purified by column chromatography through silica gel
  3. additionby volume mixture of methylene chloride and methanol as the eluent

Sources & evidence

ORD record
ord-82e17f73b8e5421aa8e52c996a94ba1f
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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