Water → HCID 76568049, compound

HRID 1728206Notes

Reaction equation

HRID 1728206 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Br:7][C:8]1[CH:9]=[CH:10][C:11]([O:39][CH2:40][C:41]([C:44](OC)=[O:45])([CH3:43])[CH3:42])=[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]=[C:34]([Cl:36])[CH:33]=[CH:32][C:31]=3[CH3:37])[CH2:17][C:16](=[O:38])[NH:15]2)[CH:13]=1.O>C1COCC1>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([O:39][CH2:40][C:41]([CH3:43])([CH3:42])[CH2:44][OH:45])=[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]=[C:34]([Cl:36])[CH:33]=[CH:32][C:31]=3[CH3:37])[CH2:17][C:16](=[O:38])[NH:15]2)[CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 76568100HCID 76568100, compound

Product 1

HCID 76568049HCID 76568049, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

LiAlH4 (11.4 mg, 0.3 mmol) was suspended in THF in ice bath, then a solution of racemic (2′R,3R,4′S)-2′-[5-bromo-2-(2-methoxycarbonyl-2-methyl-propoxy)-phenyl]-6-chloro-4′-(5-chloro-2-methyl-phenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione prepared in Example 262d (63 mg, 0.1 mmol) in THF (2 mL) was added slowly. The reaction mixture was stirred at room temperature for 10 min, water (1 mL) was added and the resulting mixture was filtered. The filtration was concentrated and the residue was purified by Prep-HPLC to give the title compound as a white solid (Yield: 31 mg).

Workup

  1. filtrationthe resulting mixture was filtered
  2. filtrationThe filtration
  3. concentrationwas concentrated
  4. customthe residue was purified by Prep-HPLC

Sources & evidence

ORD record
ord-3cc596262ea84cdc903c0a6b2f60ce9b
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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