Pyridine → HCID 86623624, compound

HRID 1821023Notes

Reaction equation

HRID 1821023 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[C:24]([CH3:37])=[C:25]2[C:29](=[CH:30][CH:31]=1)[C@@H: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[C:24]([CH3:37])=[C:25]2[C:29](=[CH:30][CH:31]=1)[C@@H: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 86623622HCID 86623622, compound

Product 1

HCID 86623624HCID 86623624, compoundYield 309.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of pyridine (440 μL, 5.45 mmol) in dichloromethane (5.0 mL) cooled to 0° C. trifluoromethanesulfonic anhydride (840 μL, 4.99 mmol) was added. The resultant mixture was stirred for 5 min, and methyl (R or S)-(5-hydroxy-4-methyl-indan-1-yl)acetate (1.00 g, 1.34 mmol, from Step H) was added as a solid. 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 1.46 g of the title compound as a pale yellow liquid: 1H NMR (500 MHz, CDCl3) δ 1.69-1.91 (m, 1H), 2.33 (s, 3H), 2.38-2.56 (m, 2H), 2.69-2.79 (m, 1H), 2.79-3.01 (m, 2H), 3.49-3.65 (m, 1H), 3.76 (s, 3H), 7.09 (s, 2H).

Workup

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

Sources & evidence

ORD record
ord-3ffa645ee9f24670934dab049d0ea890
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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