Pyridine → HCID 131727668, compound

HRID 1821056Notes

Reaction equation

HRID 1821056 reaction equation
N1C=CC=CC=1.[F:7][C:8]([F:21])([F:20])[S:9]([O:12]S(C(F)(F)F)(=O)=O)(=[O:11])=[O:10].O[C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[CH:28]([CH2:32][C:33]([O:35][CH3:36])=[O:34])[CH2:27][CH2:26]2>ClCCl>[F:7][C:8]([F:21])([F:20])[S:9]([O:12][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[CH:28]([CH2:32][C:33]([O:35][CH3:36])=[O:34])[CH2:27][CH2:26]2)(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 53438903Methyl (5-hydroxy-2,3-dihydro-1H-inden-1-yl)acetate

Product 1

HCID 131727668HCID 131727668, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of pyridine (820 μL, 10.1 mmol) in dichloromethane (10 mL) cooled to 0° C. trifluoromethanesulfonic anhydride (1.56 mL, 9.28 mmol) was added. The resulting mixture was stirred for 5 min, and methyl (R/S)-(5-hydroxy-indan-1-yl)acetate (1.74 g, 8.44 mmol, from Step C) was added. The reaction mixture was warmed to ambient temperature, stirred for 1 hr and diluted with dichloromethane. The organic layer was washed with H2O, brine and dried over MgSO4. The mixture was filtered and concentrated in vacuo. Purification by flash chromatography (10% EtOAc/hexanes) on SiO2 gave 2.63 g of the title compound as a pale yellow liquid: 1H NMR (CDCl3) δ 1.83-1.88 (m, 1H), 2.47-2.55 (m, 2H), 2.78 (dd, 1H, J=6.0, 15.8 Hz), 2.92-3.01 (m, 2H), 3.62-3.65 (m, 1H), 3.76 (s, 3H), 7.09 (dd, 1H, J=2.3, 8.3 Hz), 7.16 (s, 1H), 7.25 (d, 1H, J=8.2 Hz).

Workup

  1. additionwas added
  2. stirringstirred for 1 hr
  3. washThe organic layer was washed with H2O, brine
  4. dry with materialdried over MgSO4
  5. filtrationThe mixture was filtered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography (10% EtOAc/hexanes) on SiO2

Sources & evidence

ORD record
ord-1f21dab656b54ea88544bbd2dda9ebe6
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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