MK 886 → 3-[1-(p-Chlorobenzyl)-3-(t-butylthio)-5-(i-propyl)-indole-2-yl]-2,2-dimethylpropanol

HRID 1090279Notes

Reaction equation

HRID 1090279 reaction equation
[Cl:1][C:2]1[CH:32]=[CH:31][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([CH:16]([CH3:18])[CH3:17])=[CH:13][CH:14]=3)[C:9]([S:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[C:8]2[CH2:24][C:25]([CH3:30])([CH3:29])[C:26](O)=[O:27])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([CH:16]([CH3:18])[CH3:17])=[CH:13][CH:14]=3)[C:9]([S:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[C:8]2[CH2:24][C:25]([CH3:30])([CH3:29])[CH2:26][OH:27])=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 3651377MK 886HCID 21226445Aluminium lithium hydride

Product 1

HCID 150354093-[1-(p-Chlorobenzyl)-3-(t-butylthio)-5-(i-propyl)-indole-2-yl]-2,2-dimethylpropanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 200 mg of methyl 1-(p-chlorobenzyl) -3-(t-butylthio)-α,α-dimethyl -5-(i-propyl)-indole-2-propanoate (from Example 25) in 1.5 mL tetrahydrofuran (THF) was added 0.4 ml of a solution of lithium aluminum hydride (1.0M in THF) at 0° C. After 2 h at 0° C., the reaction mixture was quenched with saturated aqueous Na2SO4, diluted with ether and stirred at room temperature for 1 h. The resultant slurry was filtered and the filtrate concentrated to dryness. The resultant oil was purified by flash chromatography (eluant: hexane ethyl acetate, 8:2) to give the title compound as a viscous oil.

Workup

  1. customthe reaction mixture was quenched with saturated aqueous Na2SO4
  2. additiondiluted with ether
  3. filtrationThe resultant slurry was filtered
  4. concentrationthe filtrate concentrated to dryness
  5. customThe resultant oil was purified by flash chromatography (eluant: hexane ethyl acetate, 8:2)

Sources & evidence

ORD record
ord-71c6d783dc3245c18654e817131d5577
Source dataset
uspto-grants-1992_01
Patent number
US05081138

Reaction notes

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