Methanol → HCID 70563490, compound

HRID 1427222Notes

Reaction equation

HRID 1427222 reaction equation
[Li+].[BH4-].CO.[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([N:19]2[C:27]3[C:22](=[C:23]([N:28]4[C:32]([CH3:33])=[CH:31][CH:30]=[C:29]4[CH3:34])[CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20]2)([CH2:17][CH3:18])[C:13](OC)=[O:14])=[CH:8][CH:7]=1>C1COCC1>[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([N:19]2[C:27]3[C:22](=[C:23]([N:28]4[C:32]([CH3:33])=[CH:31][CH:30]=[C:29]4[CH3:34])[CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20]2)([CH2:17][CH3:18])[CH2:13][OH:14])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 70562744HCID 70562744, compound

Product 1

HCID 70563490HCID 70563490, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of LiBH4 (22 mg) in THF (3 mL) was added MeOH (32 mg, 5.43 mmol) and a solution of methyl 2-(4-chlorophenyl)-2-(4-(2,5-dimethyl-1H-pyrrol-1-yl)-1H-indol-1-yl)butanoate (105 mg) in THF (3 mL). The mixture was stirred at room temperature for 2 h. The solution was quenched with saturated ammonium chloride solution, and extracted with ethyl acetate (20 mL). The organic layer was washed with brine, dried over sodium sulfate, and evaporated. The residue was purified by chromatography on silica gel (25-35% ethyl acetate in hexanes) to afford the title compound as a pale yellow solid. LC/MS m/z=393.2 [M+H]+.

Workup

  1. customThe solution was quenched with saturated ammonium chloride solution
  2. extractionextracted with ethyl acetate (20 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe residue was purified by chromatography on silica gel (25-35% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-7319b7d2018d4324b7cc75833565b9ca
Source dataset
uspto-grants-2015_01
Patent number
US08933113B2

Reaction notes

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