Aluminium lithium hydride → HCID 76567920, compound

HRID 1728225Notes

Reaction equation

HRID 1728225 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Br:7][C:8]1[CH:9]=[CH:10][C:11]([O:38][CH2:39][C:40]([C:43](OC)=[O:44])([CH3:42])[CH3:41])=[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>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([O:38][CH2:39][C:40]([CH3:42])([CH3:41])[CH2:43][OH:44])=[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

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 76567902HCID 76567902, compound

Product 1

HCID 76567920HCID 76567920, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a mixture of LiAlH4 (10 mg, 0.26 mmol) in diethyl ether (2 mL) was added racemic (2′R,3R,4′S)-2′-[5-bromo-2-(2-methoxycarbonyl-2-methyl-propoxy)-phenyl]-6-chloro-4′-(3-chlorophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione prepared in Example 276b (40 mg, 0.062 mmol). The mixture was stirred at room temperature for 10 min, quenched with methanol, purified by Prep-HPLC to give title compound (16 mg, 42%). m/z (M+H)+: 617

Workup

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

Sources & evidence

ORD record
ord-75a64f15c06349c4bad5020a15144f38
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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