1-t-Butoxycarbonyl-3-{2-[2-(3-methoxyphenyl)ethyl]phenoxy}piperidine → 3-{2-[2-(3-Methoxyphenyl)ethyl]phenoxy}-1-methylpiperidine

HRID 743272Notes

Reaction equation

HRID 743272 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=2)[CH2:9]1)=O)(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[CH3:30][O:29][C:25]1[CH:24]=[C:23]([CH2:22][CH2:21][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[O:14][CH:10]2[CH2:11][CH2:12][CH2:13][N:8]([CH3:6])[CH2:9]2)[CH:28]=[CH:27][CH:26]=1

Participants

3

Reactant 2

HCID 105017801-t-Butoxycarbonyl-3-{2-[2-(3-methoxyphenyl)ethyl]phenoxy}piperidineHCID 21226445Aluminium lithium hydride

Product 1

HCID 105947823-{2-[2-(3-Methoxyphenyl)ethyl]phenoxy}-1-methylpiperidineYield 51.7%

Procedure

Following a procedure similar to that described in Example 38, 880 mg of 1-t-butoxycarbonyl-3-{2-[2-(3-methoxyphenyl)ethyl]phenoxy}piperidine [prepared as described in Example 51(a)] were reacted with 162 mg of lithium aluminum hydride. 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 360 mg (yield 51%) 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-d046056e518e48c8942edb7a1c75c56b
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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