Aluminium lithium hydride → HCID 54185493, compound

HRID 1456565Notes

Reaction equation

HRID 1456565 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][CH2:7][CH2:8][C@@H:9]2[CH2:13][C@@H:12]([OH:14])[CH2:11][N:10]2[C:15](OCC)=O)=[C:4]([CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][CH2:7][CH2:8][C@@H:9]2[CH2:13][C@@H:12]([OH:14])[CH2:11][N:10]2[CH3:15])=[C:4]([CH2:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 54296142HCID 54296142, compound

Product 1

HCID 54185493HCID 54185493, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

260 mg of (2R,4R)-2-{2-[4-chloro-2-(2-phenylethyl)phenoxy]ethyl}-1-ethoxycarbonyl-4-hydroxypyrrolidine [prepared as described in step (a) above], 10 ml of tetrahydrofuran and 70 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 103 mg (yield 46%) of the title compound as a colorless solid substance, melting at 65°-68° C.

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-e409ecc2a7ff436f8e99b8c9b75517d5
Source dataset
uspto-grants-1998_12
Patent number
US05843983

Reaction notes

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