Tetrabutylammonium Fluoride → 1289023-89-7

HRID 409033Notes

Reaction equation

HRID 409033 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:19][CH2:18][C@@H:17]([O:20][Si](C(C)C)(C(C)C)C(C)C)[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[C:10]1=[O:31].CCCC[N+](CCCC)(CCCC)CCCC.[F-].C(OCC)(=O)C.CCCCCC>O1CCCC1>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@@H:9]1[CH2:19][CH2:18][C@@H:17]([OH:20])[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[C:10]1=[O:31]

Participants

5

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 21226206Ethyl acetate hexaneHCID 66811345HCID 66811345, compound

Product 1

HCID 584679831289023-89-7Yield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-15 °C

Procedure

In a 250 mL round-bottom flask was dissolved (9R)-6-(2,3-difluorophenyl)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-one (0.218 g, 0.49 mmol) in tetrahydrofuran (5 mL) to give a colorless solution. After cooling to −15° C. (ice-methanol bath) under nitrogen, TBAF (0.490 mL, 0.490 mmol) was added, and the resulting bright yellow solution was stirred at −15° C. for 1 h. It was quenched with sodium bicarbonate solution and diluted with ethyl acetate. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers was washed with brine, dried and concentrated to give a tan oil. Flash column chromatography (25 g silica gel column) up to 100% ethyl acetate/hexane afforded the desired product (112 mg, 62%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.53 (dd, J=4.91, 1.64 Hz, 1H) 7.85 (dd, J=7.68, 1.64 Hz, 1H) 7.34 (dd, J=7.68, 4.91 Hz, 1H) 7.00-7.16 (m, 3H) 5.32 (s, 1H) 4.94-5.04 (m, 1H) 4.48 (dd, J=11.83, 3.02 Hz, 1H) 2.14-2.48 (m, 4H); 19F NMR (376 MHz, CHLOROFORM-d) δ ppm −138.24-−138.07 (m, 1F) −140.70-−140.50 (m, 1F).

Workup

  1. customto give a colorless solution
  2. customIt was quenched with sodium bicarbonate solution
  3. additiondiluted with ethyl acetate
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washThe combined organic layers was washed with brine
  7. customdried
  8. concentrationconcentrated
  9. customto give a tan oil

Sources & evidence

ORD record
ord-b93c896186c74ef6a1d06a86f20cccd3
Source dataset
uspto-grants-2014_06
Patent number
US08759372B2

Reaction notes

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