4-t-Butoxycarbonyl-2-{2-[2-(3-methoxyphenyl)ethyl]phenoxymethyl}morpholine → 2-{2-[2-(3-Methoxyphenyl)ethyl]phenoxymethyl}-4-methylmorpholine

HRID 743261Notes

Reaction equation

HRID 743261 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][O: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-]>O1CCCC1>[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[O:11][CH2:12][CH2:13][N:8]([CH3:6])[CH2:9]2)[CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 107173794-t-Butoxycarbonyl-2-{2-[2-(3-methoxyphenyl)ethyl]phenoxymethyl}morpholineHCID 21226445Aluminium lithium hydride

Product 1

HCID 105957852-{2-[2-(3-Methoxyphenyl)ethyl]phenoxymethyl}-4-methylmorpholineYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following a procedure similar to that described in Example 38, 870 mg of 4-t-butoxycarbonyl-2-{2-[2-(3-methoxyphenyl)ethyl]phenoxymethyl}morpholine [prepared as described in Example 45(a)] were reacted with a dispersion of 113 mg of lithium aluminum hydride in 15 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 620 mg (yield 94%) 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-193d48f91b4949fd8cfcbf4bfbd57360
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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