Aluminium lithium hydride → (R)-2-{2-[2-(3-Methoxyphenyl)ethyl]phenoxymethyl}-1-methylpyrrolidine

HRID 743322Notes

Reaction equation

HRID 743322 reaction equation
C(O[C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H: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][CH3:30])[CH:24]=1)=O)(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[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][CH2:13][C@H: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 21226445Aluminium lithium hydrideHCID 53745429(R)-1-t-Butoxycarbonyl-2-{2-[2-(3-methoxyphenyl) ethyl]phenoxymethyl}pyrrolidine

Product 1

HCID 53979546(R)-2-{2-[2-(3-Methoxyphenyl)ethyl]phenoxymethyl}-1-methylpyrrolidineYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following a procedure similar to that described in Example 38(a), 1.00 g of (R)-1-t-butoxycarbonyl-2-{2-[2-(3-methoxyphenyl)ethyl]phenoxymethyl}pyrrolidine [prepared as described in Example 76(a)] was reacted with 0.184 g of lithium aluminum hydride dispersed in 10 ml of tetrahydrofuran. The mixture was then worked up as described in Example 38(a), and the crude product thus obtained was purified by column chromatography through silica gel, using a 20:1 by volume mixture of methylene chloride and methanol as the eluent, to give 0.750 g (yield 95%) 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-ab7f78b08ddd4f12b64f181f2b06b2d8
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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