Aluminium lithium hydride → HCID 76568073, compound

HRID 1728180Notes

Reaction equation

HRID 1728180 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:33][CH2:34][C:35]([C:38](OC)=[O:39])([CH3:37])[CH3:36])=[C:6]([CH:8]2[CH2:13][C:12](=[O:14])[NH:11][CH:10]([C:15]3[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=3[CH3:22])[C:9]32[C:30]2[C:25](=[CH:26][C:27]([Cl:31])=[CH:28][CH:29]=2)[NH:24][C:23]3=[O:32])[CH:7]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:33][CH2:34][C:35]([CH3:37])([CH3:36])[CH2:38][OH:39])=[C:6]([CH:8]2[CH2:13][C:12](=[O:14])[NH:11][CH:10]([C:15]3[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=3[CH3:22])[C:9]32[C:30]2[C:25](=[CH:26][C:27]([Cl:31])=[CH:28][CH:29]=2)[NH:24][C:23]3=[O:32])[CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 76568186HCID 76568186, compound

Product 1

HCID 76568073HCID 76568073, compoundYield 11.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a manner similar to the method described in Example 231, racemic (2′S,3S,4′R)-4′-[5-bromo-2-(2-methoxycarbonyl-2-methyl-propoxy)-phenyl]-6-chloro-2′-(5-fluoro-2-methyl phenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (120 mg, 0.187 mmol) was reacted with LiAlH4 (35 mg, 0.934 mmol) in THF and the crude product was purified by Prep-HPLC to give title compound as a white solid (13 mg).

Workup

  1. customthe crude product was purified by Prep-HPLC

Sources & evidence

ORD record
ord-139913a3d5ea49ddb49a18d252e946bd
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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