Aluminium lithium hydride → HCID 67583627, compound

HRID 1456553Notes

Reaction equation

HRID 1456553 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]=[CH:19][C:18]([F:21])=[CH:17][C:16]=1[CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[C:26]([O:31][CH3:32])[CH:25]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[F:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][CH2:13][CH2:12][C@@H:7]2[CH2:8][C@@H:9]([OH:11])[CH2:10][N:6]2[CH3:4])=[C:16]([CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[C:26]([O:31][CH3:32])[CH:25]=2)[CH:17]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67584131HCID 67584131, compound

Product 1

HCID 67583627HCID 67583627, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

551 mg of (2R,4R)-1-ethoxycarbonyl-2-[2-{4-fluoro-2-[2-(4-fluoro-3-methoxyphenyl)ethyl]phenoxy}ethyl]-4-hydroxypyrrolidine [prepared as described in step (a) above], 20 ml of tetrahydrofuran and 140 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 concentrate thus obtained was purified by silica gel column chromatography, using a 3:2 by volume mixture of methylene chloride and methanol as the eluent, to give 405 mg (yield 84%) of the title compound as a colorless oily substance.

Workup

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

Sources & evidence

ORD record
ord-5941fc6c72f749708c67720bc6c10abc
Source dataset
uspto-grants-1998_12
Patent number
US05843983

Reaction notes

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