Tetrabutylammonium Fluoride → HCID 67006557, compound

HRID 564348Notes

Reaction equation

HRID 564348 reaction equation
C([Si]([O:8][CH:9]1[CH2:25][CH2:24][CH:13]2[CH2:14][O:15][C:16]3[C:21]([C:12]2([S:26]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)(=[O:28])=[O:27])[CH2:11][CH2:10]1)=[C:20]([F:22])[CH:19]=[CH:18][C:17]=3[F:23])(C)C)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].CCOC(C)=O.C(Cl)Cl>C1COCC1>[Cl:35][C:32]1[CH:31]=[CH:30][C:29]([S:26]([C:12]23[CH2:11][CH2:10][CH:9]([OH:8])[CH2:25][CH2:24][CH:13]2[CH2:14][O:15][C:16]2[C:21]3=[C:20]([F:22])[CH:19]=[CH:18][C:17]=2[F:23])(=[O:28])=[O:27])=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 21226138Dichloromethane ethylacetateHCID 67006489HCID 67006489, compound

Product 1

HCID 67006557HCID 67006557, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl-[11a-(4-chloro-benzenesulfonyl)-1,4-difluoro-6,6a,7,8,9,10,11,11a-octahydro-cyclohepta[c]chromen-9-yloxy]-dimethyl-silane (700 mg, 1.30 mmol) in THF (10 mL) at 0° C. was treated with TBAF (1 M in THF, 2.6 mL, 2.6 mmol) and warmed to ambient temperature. After 12 h, the reaction mixture was quenched with saturated aqueous NH4Cl and extracted with EtOAc (2×). The combined organic extracts were washed with saturated aqueous NaHCO3, brine, dried over MgSO4 and concentrated in vacuo. Flash chromatography (2→20% EtOAc/CH2Cl2) afforded Example 344A1 (200 mg, Rf=0.49, 10% EtOAc/CH2Cl2): 1H NMR (CDCl3 400 MHz) δ 7.61 (d, J=8.7 Hz, 2H), 7.49 (d, J=8.7 Hz, 2H), 7.04 (m, 1H), 6.40 (m, 1H), 5.13 (dd, J=11.7, 2.2 Hz, 1H), 4.26 (dd, J=11.0, 2.2 Hz, 1H), 4.14 (m, 1H), 2.85 (d, J=6.6 Hz, 1H), 2.52 (ddd, J=14.6, 10.3, 2.2 Hz, 1H), 2.34 (m, 1H), 2.22 (m, 1H), 1.87-1.62 (m, 5H); followed by Example 344B1 (130 mg, Rf=0.33, 10% EtOAc/CH2Cl2): 1H NMR (CDCl3 400 MHz) δ 7.64 (d, J=8.8 Hz, 2H), 7.50 (d, J=8.8 Hz, 2H), 7.04 (m, 1H), 6.40 (m, 1H), 5.13 (dd, J=11.0, 2.2 Hz, 1H), 4.26 (dd, J=11.7, 2.2 Hz, 1H), 3.67 (m, 1H), 2.96 (m, 1H), 2.75 (m, 1H), 2.19 (m, 1H), 2.02 (m, 1H), 1.81-1.49 (m, 5H).

Workup

  1. customthe reaction mixture was quenched with saturated aqueous NH4Cl
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organic extracts were washed with saturated aqueous NaHCO3, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customFlash chromatography (2→20% EtOAc/CH2Cl2) afforded Example 344A1 (200 mg, Rf=0.49, 10% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-0ae24637d9ab4c05bb2b488d4a7ec17c
Source dataset
uspto-grants-2011_11
Patent number
US08067621B2

Reaction notes

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