Tetrabutylammonium Fluoride → HCID 21099269, compound

HRID 1351738Notes

Reaction equation

HRID 1351738 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][C:9]1([CH2:31][CH2:32][CH3:33])[C:14]2[NH:15][C:16]3[C:21]([C:13]=2[CH2:12][CH2:11][O:10]1)=[C:20]([C:22]([N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)=[O:23])[CH:19]=[CH:18][C:17]=3[F:30])(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CCOC(C)=O>[F:30][C:17]1[CH:18]=[CH:19][C:20]([C:22]([N:24]2[CH2:25][CH2:26][O:27][CH2:28][CH2:29]2)=[O:23])=[C:21]2[C:16]=1[NH:15][C:14]1[C:9]([CH2:8][CH2:7][OH:6])([CH2:31][CH2:32][CH3:33])[O:10][CH2:11][CH2:12][C:13]2=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 21099114HCID 21099114, compound

Product 1

HCID 21099269HCID 21099269, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of {1-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-8-fluoro-1-propyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-5-yl}-morpholin-4-yl-methanone (350 mg, 0.693 mmol) in THF (5 mL) was added TBAF (0.832 mL of 1.0 M in THF, 0.832 mmol) at room temperature. After stirring for 4 hours at room temperature, the reaction mixture was diluted with EtOAc (20 mL). The organic solution was washed with 0.5 N HCl (20 mL) and brine (20 mL), dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (silica, 50% EtOAc in hexanes) to give 254 mg (94%) of [8-fluoro-1-(2-hydroxy-ethyl)-1-propyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-5-yl]-morpholin-4-yl-methanone as white solid.

Workup

  1. washThe organic solution was washed with 0.5 N HCl (20 mL) and brine (20 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography (silica, 50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-c60b1cc0d804409689c2decab310f084
Source dataset
uspto-grants-2007_05
Patent number
US07217730B2

Reaction notes

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