Aluminium lithium hydride → HCID 58413055, compound

HRID 240597Notes

Reaction equation

HRID 240597 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:9]=1[O:10][C@@H:11]1[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@H:13]([C:23](OC)=[O:24])[CH2:12]1>C1COCC1>[NH2:7][C:8]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:9]=1[O:10][C@@H:11]1[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:21])([CH3:22])[CH3:20])=[O:17])[C@H:13]([CH2:23][OH:24])[CH2:12]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 58413225HCID 58413225, compound

Product 1

HCID 58413055HCID 58413055, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (540.0 mg) added to a cooled (0-4° C.) solution of (2S,4S)-1-tert butyl 2-methyl 4-(2-amino-5-fluorophenoxy)pyrrolidine-1,2-dicarboxylate (3.36 g) in THF (30.0 ml). The reaction mixture was stirred at this temperature for 4 h. After this time the mixture was quenched with water (0.54 ml), NaOH (2M; 0.54 ml) and water (3×0.54 ml). The mixture was stirred for 1.5 h, then diluted with EtOAc and MgSO4 was added. The suspension was filtered through celite and the filtrate evaporated. The residue was purified by chromatography.

Workup

  1. customAfter this time the mixture was quenched with water (0.54 ml), NaOH (2M; 0.54 ml) and water (3×0.54 ml)
  2. stirringThe mixture was stirred for 1.5 h
  3. additiondiluted with EtOAc and MgSO4
  4. additionwas added
  5. filtrationThe suspension was filtered through celite
  6. customthe filtrate evaporated
  7. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-5ddc4b9e3af44d028c2df5f48db279b8
Source dataset
uspto-grants-2014_02
Patent number
US08648068B2

Reaction notes

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