Aluminium lithium hydride → HCID 53862865, compound

HRID 1456567Notes

Reaction equation

HRID 1456567 reaction equation
C(O[C:4]([N:6]1[CH2:10][C@H:9]([OH:11])[CH2:8][C@H:7]1[CH2:12][CH2:13][O:14][C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:16]=1[CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[OH:11][C@H:9]1[CH2:10][N:6]([CH3:4])[C@H:7]([CH2:12][CH2:13][O:14][C:15]2[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:16]=2[CH2:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:8]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 54342584HCID 54342584, compound

Product 1

HCID 53862865HCID 53862865, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1150 mg of (2R,4R)-1-ethoxycarbonyl-4-hydroxy-2-{2-[5-methyl-2-(2-phenylethyl)phenoxy]ethyl}pyrrolidine [prepared as described in step (b) above], 18 ml of tetrahydrofuran and 330 mg of lithium aluminum hydride were allowed to react together and subsequently treated in the same manner as described in step (b) of Example 1. The concentrated substance thus obtained was purified by silica gel column chromatography, using a 10:1 by volume mixture of methylene chloride and methanol as the eluent, to give 776 mg (yield 80%) of the title compound as a colorless solid substance.

Workup

  1. customto react together
  2. additionsubsequently treated in the same manner
  3. customThe concentrated substance thus obtained
  4. customwas purified by silica gel column chromatography
  5. additionby volume mixture of methylene chloride and methanol as the eluent

Sources & evidence

ORD record
ord-679e1dc19b3e4120ad3a0e46ff0c5a85
Source dataset
uspto-grants-1998_12
Patent number
US05843983

Reaction notes

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