Water → HCID 86724035, compound

HRID 1475491Notes

Reaction equation

HRID 1475491 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[CH:15]=[C:14]([CH:17]([OH:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:13]=[CH:12][C:11]=2[C:10]([CH3:26])([CH3:25])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:29]I.O>C1COCC1>[C:1]([O:5][C:6]([N:8]1[C:16]2[CH:15]=[C:14]([CH:17]([O:24][CH3:29])[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:13]=[CH:12][C:11]=2[C:10]([CH3:26])([CH3:25])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 70980819HCID 70980819, compound

Product 1

HCID 86724035HCID 86724035, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-(hydroxy-phenyl-methyl)-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester (0.15 g, 0.42 mmol) in THF (5 mL) was added sodium hydride (60%, 0.02 g, 0.50 mmol) and the mixture was stirred for 1 h. Methyl iodide (52 μL, 0.84 mmol) was added and the reaction mixture was stirred for 18 h at ambient temperature. Water (10 mL) was added and the product was extracted with EtOAc (2×10 mL). The combined organic phase was dried (MgSO4) and evaporated in vacuo to give an oil. Chromatography (SiO2; gradient elution with 0-70% EtOAc in 40-60 petroleum ether) gave the title compound (0.11 g, 70%) as an oil. MS: [M+H]+=369.

Workup

  1. stirringthe reaction mixture was stirred for 18 h at ambient temperature
  2. extractionthe product was extracted with EtOAc (2×10 mL)
  3. dry with materialThe combined organic phase was dried (MgSO4)
  4. customevaporated in vacuo
  5. customto give an oil
  6. washChromatography (SiO2; gradient elution with 0-70% EtOAc in 40-60 petroleum ether)

Sources & evidence

ORD record
ord-402c566d3523414995562cba5506ae02
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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