Aluminium lithium hydride → HCID 76568180, compound

HRID 1728227Notes

Reaction equation

HRID 1728227 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Br:7][C:8]1[CH:9]=[CH:10][C:11]([O:38][C:39]([C:42](OCC)=[O:43])([CH3:41])[CH3:40])=[C:12]([CH:14]2[C:19]3([C:27]4[C:22](=[CH:23][C:24]([Cl:28])=[CH:25][CH:26]=4)[NH:21][C:20]3=[O:29])[CH:18]([C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[CH:31]=3)[CH2:17][C:16](=[O:37])[NH:15]2)[CH:13]=1>C(OCC)C>[Cl:28][C:24]1[CH:23]=[C:22]2[NH:21][C:20](=[O:29])[C:19]3([CH:18]([C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[CH:31]=4)[CH2:17][C:16](=[O:37])[NH:15][CH:14]3[C:12]3[CH:13]=[C:8]([Br:7])[CH:9]=[CH:10][C:11]=3[O:38][C:39]([CH3:40])([CH3:41])[CH2:42][OH:43])[C:27]2=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 76567937HCID 76567937, compound

Product 1

HCID 76568180HCID 76568180, compoundYield 38.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a mixture of LiAlH4 (2.5 mg, 0.066 mmol) in diethyl ether (1 mL) was added racemic (2′R,3R,4′S)-2′-[5-bromo-2-(1-ethoxycarbonyl-1-methyl-ethoxy)-phenyl]-6-chloro-4′-(3-chlorophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (10 mg, 0.016 mmol). The mixture was stirred at room temperature for 10 min, quenched with MeOH, purified by Prep-HPLC to give product (3.7 mg, 38%). (M+H)+: 603

Workup

  1. customquenched with MeOH
  2. custompurified by Prep-HPLC

Sources & evidence

ORD record
ord-231a4fa91c6b4cffa873a1a90230d5c1
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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