Tetrabutylammonium Fluoride → HCID 66811007, compound

HRID 1666150Notes

Reaction equation

HRID 1666150 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[F:19][C:20]1[C:25]([F:26])=[CH:24][CH:23]=[CH:22][C:21]=1[C@@H:27]1[CH2:38][CH2:37][C@@H:36]([O:39][Si](C(C)C)(C(C)C)C(C)C)[C:30]2=[N+:31]([O-:35])[CH:32]=[CH:33][CH:34]=[C:29]2[CH2:28]1>C1COCC1>[F:19][C:20]1[C:25]([F:26])=[CH:24][CH:23]=[CH:22][C:21]=1[C@@H:27]1[CH2:38][CH2:37][C@@H:36]([OH:39])[C:30]2=[N+:31]([O-:35])[CH:32]=[CH:33][CH:34]=[C:29]2[CH2:28]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66811086HCID 66811086, compound

Product 1

HCID 66811007HCID 66811007, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (4.18 mL, 4.18 mmol) was added to the THF (10 mL) solution of (6R,9R)-6-(2,3-difluorophenyl)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine 1-oxide (1.56 g, 3.48 mmol) at rt. The reaction was stirred at room temperature for 2 hours and LCMS showed that the reaction was completed. The solvent was removed via vacuum and the crude was load to flash column and eluted with methanol in CH2Cl2 from 0 to 10% to afford the desired product (0.7662 g, 75%) as a yellow solid. MS(ESI)[M+H+]=292. 10; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.16-8.26 (m, 1H) 7.14-7.20 (m, 1H) 6.98-7.12 (m, 3H) 6.90 (td, J=7.55, 1.76 Hz, 1H) 5.38-5.48 (m, 1H) 3.24-3.47 (m, 2H) 3.02 (dd, J=14.60, 1.76 Hz, 1H) 2.27-2.44 (m, 3H) 1.79-1.94 (m, 1H).

Workup

  1. customThe solvent was removed via vacuum
  2. washeluted with methanol in CH2Cl2 from 0 to 10%

Sources & evidence

ORD record
ord-b9808b25e1da4a49b8c2ef74d617980a
Source dataset
uspto-grants-2011_10
Patent number
US08044043B2

Reaction notes

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