HCID 19424011, compound → HCID 19423847, compound

HRID 743255Notes

Reaction equation

HRID 743255 reaction equation
C(O[C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH2:30][O:31][CH3:32])[CH:24]=1)=O)(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:32][O:31][CH2:30][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][CH2:13][CH:9]2[CH2:10][CH2:11][CH2:12][N:8]2[CH3:6])[CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 19424011HCID 19424011, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19423847HCID 19423847, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following a procedure similar to that described in Example 38, 1.00 g of 1-t-butoxycarbonyl-2-{2-[2-(3-methoxymethoxyphenyl)ethyl]phenoxymethyl}pyrrolidine [prepared in a similar manner to that described in Example 40(a)] was reacted with a dispersion of 88.1 mg of lithium aluminum hydride in 10 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 68 mg (yield 83%) of the title compound as a colorless oil.

Workup

  1. customprepared in a similar manner to that
  2. customthe crude product thus obtained
  3. customwas purified by column chromatography through silica gel
  4. additionby volume mixture of methylene chloride and methanol as the eluent

Sources & evidence

ORD record
ord-a5f2a0cdb6f04d1680a2c0a01d10e9bc
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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