Aluminium lithium hydride → HCID 53666918, compound

HRID 1456588Notes

Reaction equation

HRID 1456588 reaction equation
CN(C)C([O:5][C@H:6]1[CH2:10][N:9]([C:11](OCCCCCCCC)=O)[C@H:8]([CH2:22][CH2:23][O:24][C:25]2[C:30]([F:31])=[CH:29][CH:28]=[CH:27][C:26]=2[CH2:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:7]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[F:31][C:30]1[C:25]([O:24][CH2:23][CH2:22][C@@H:8]2[CH2:7][C@@H:6]([OH:5])[CH2:10][N:9]2[CH3:11])=[C:26]([CH2:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 54165020HCID 54165020, compound

Product 1

HCID 53666918HCID 53666918, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

984 mg of (2R,4R)-4-dimethylcarbamoyloxy-2-{2-[6-fluoro-2-(2-phenylethyl)phenoxy]ethyl}-1-octyloxycarbonylpyrrolidine [prepared as described in step (a) above], 20 ml of tetrahydrofuran and 200 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 5:1 by volume mixture of methylene chloride and methanol as the eluent, to give 319 mg (yield 53%) of the title compound as an oily 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-aac41a85bd3e4fe1983f82c4e465cdde
Source dataset
uspto-grants-1998_12
Patent number
US05843983

Reaction notes

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