Aluminium lithium hydride → (4R)-4-Hydroxy-1-methyl-2-[2-(2-phenylethyl)phenoxymethyl]pyrrolidine

HRID 743300Notes

Reaction equation

HRID 743300 reaction equation
C(O[C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][CH:9]1[CH2:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=O)(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[OH:13][C@H:11]1[CH2:12][N:8]([CH3:6])[CH:9]([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:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:10]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 54118331(4R)-1-t-butoxycarbonyl-4-hydroxy-2-[2-(2-phenylethyl)phenoxymethyl]pyrrolidine

Product 1

HCID 54021671(4R)-4-Hydroxy-1-methyl-2-[2-(2-phenylethyl)phenoxymethyl]pyrrolidineYield 63.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following a procedure similar to that described in Example 38, 300 mg of (4R)-1-t-butoxycarbonyl-4-hydroxy-2-[2-(2-phenylethyl)phenoxymethyl]pyrrolidine [prepared as described in Example 65(b)] were reacted with 85.9 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 150 mg (yield 63%) 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-82557143a4c44b10af182ae7deaecac3
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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