Tetrahydrofuran → HCID 71559418, compound

HRID 1529246Notes

Reaction equation

HRID 1529246 reaction equation
[C:1]12([C:11]([N:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]([OH:23])[CH2:15][CH2:14]3)=[O:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[H-].[Na+].[CH2:26]1COC[CH2:27]1>O>[C:1]12([C:11]([N:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]([O:23][CH2:26][CH3:27])[CH2:15][CH2:14]3)=[O:12])[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 72709167HCID 72709167, compound

Product 1

HCID 71559418HCID 71559418, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.1 g (0.32 mmol) adamantan-1-yl-(4-hydroxy-3,4-dihydro-2H-quinolin-1-yl)-methanone and 35 mg (55% in oil, 0.8 mmol) NaH in 5 mL THF at 0° C. was treated with 0.15 g (0.99 mmol) iododethane and allowed to stir to room temperature and subsequently heated to 50° C. overnight. The mixture was diluted with water and extracted with ethyl acetate. The combined organic phases were dried with MgSO4, filtered and evaporated. The residue was subjected to column chromatography on reversed phase eluting with a gradient formed from acetonitrile, water and formic acid to yield after evaporation of the product containing fractions 24.5 mg (22%) of the title compound as colourless solid. MS(m/e): 340.3 (MH+).

Workup

  1. additionwas treated with 0.15 g (0.99 mmol) iododethane
  2. temperaturesubsequently heated to 50° C. overnight
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic phases were dried with MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. washeluting with a gradient
  8. customformed from acetonitrile, water and formic acid
  9. customto yield
  10. customafter evaporation of the product
  11. additioncontaining fractions 24.5 mg (22%) of the title compound as colourless solid

Sources & evidence

ORD record
ord-aee795a103bd47cfa034d7ec9e92503e
Source dataset
uspto-grants-2015_07
Patent number
US09090615B2

Reaction notes

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