Aluminium lithium hydride → HCID 67863336, compound

HRID 2073268Notes

Reaction equation

HRID 2073268 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:15][C@H:14]([NH:16][S:17]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[CH2:13][C@H:12]2/[CH:27]=[CH:28]\[CH2:29][CH2:30][CH2:31][C:32](OC)=[O:33])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:15][C@H:14]([NH:16][S:17]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[CH2:13][C@H:12]2/[CH:27]=[CH:28]\[CH2:29][CH2:30][CH2:31][CH2:32][OH:33])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67863345HCID 67863345, compound

Product 1

HCID 67863336HCID 67863336, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (2S,4R)-1-(4-chlorophenylsulfonyl)-4-(4-chlorophenylsulfonylamino)-2-[(Z)-5-methoxycarbonyl-1-pentenyl]pyrrolidine 500 mg) in dry tetrahydrofuran (20 ml) was added lithium aluminum hydride (34 mg) under ice bath cooling. After the mixture was stirred in an ice bath for 30 minutes, aqueous tetrahydrofuran was added thereto and the mixture was filtered through Celite. The filtrate was washed successively with water and brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was solidified with ether to give (2S,4R)-1-(4-chlorophenylsulfonyl)-4-(4-chlorophenylsulfonylamino)-2-[(Z)-6-hydroxy-1-hexenyl]pyrrolidine (350 mg).

Workup

  1. temperaturecooling
  2. filtrationthe mixture was filtered through Celite
  3. washThe filtrate was washed successively with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-65f5eba021a74c8fad6d5400cdf7623f
Source dataset
uspto-grants-1990_04
Patent number
US04916152

Reaction notes

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