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

HRID 743268Notes

Reaction equation

HRID 743268 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=2)[CH2:9]1)=O)(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[CH3:31][O:30][C:26]1[CH:25]=[C:24]([CH2:23][CH2:22][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[O:15][CH2:14][CH:10]2[CH2:11][CH2:12][CH2:13][N:8]([CH3:6])[CH2:9]2)[CH:29]=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 117966521-t-Butoxycarbonyl-3-{2-[2-(3-methoxyphenyl)ethyl]phenoxymethyl}piperidineHCID 21226445Aluminium lithium hydride

Product 1

HCID 100885823-{2-[2-(3-Methoxyphenyl)ethyl]phenoxymethyl}-1-methylpiperidineYield 76.7%

Procedure

Following a procedure similar to that described in Example 38, 850 mg of 1-t-butoxycarbonyl-3-{2-[2-(3-methoxyphenyl) ethyl]phenoxymethyl}piperidine (prepared as described in Example 49) were reacted with 113 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 520 mg (yield 76%) of the title compound as a solid.

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-f010549bcf9b4a2885c7ada0c52ec7b2
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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