Tetrabutylammonium Fluoride → Mevidalen

HRID 1854563Notes

Reaction equation

HRID 1854563 reaction equation
[Si]([O:8][CH2:9][C@H:10]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[CH2:20][CH2:21][C:22]([OH:25])([CH3:24])[CH3:23])[C@H:12]([CH3:26])[N:11]1[C:27](=[O:37])[CH2:28][C:29]1[C:34]([Cl:35])=[CH:33][CH:32]=[CH:31][C:30]=1[Cl:36])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[Cl:36][C:30]1[CH:31]=[CH:32][CH:33]=[C:34]([Cl:35])[C:29]=1[CH2:28][C:27]([N:11]1[C@@H:10]([CH2:9][OH:8])[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[CH2:20][CH2:21][C:22]([OH:25])([CH3:23])[CH3:24])[C@@H:12]1[CH3:26])=[O:37]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 1234269101-[(1S,3R)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-(3-hydroxy-3-methylbutyl)-1-methyl-3,4-dihydroisoquinolin-2(1H)-yl]-2-(2,6-dichlorophenyl)ethanone

Product 1

HCID 86290953MevidalenYield 92.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 1-[(1S,3R)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-(3-hydroxy-3-methylbutyl)-1-methyl-3,4-dihydroisoquinolin-2(1H)-yl]-2-(2,6-dichlorophenyl)ethanone (0.16 g, 0.28 mmol) in THF (2.8 mL). Add tetrabutylammonium fluoride (0.30 mL, 0.30 mmol, 1M in THF). Stir 40 min. Add saturated ammonium chloride solution and extract with ethyl acetate. Combine the ethyl acetate extracts; wash with water and brine, dry over sodium sulfate, filter, and concentrate under reduced pressure to give a residue. Purify the residue by silica gel chromatography, eluting with ethyl acetate: hexanes (gradient, 0-60%) to give the title compound as a white foam (0.12 g, 0.26 mmol). MS (m/z): 450 (M+1).

Workup

  1. extractionAdd saturated ammonium chloride solution and extract with ethyl acetate
  2. washwash with water and brine
  3. dry with materialdry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate under reduced pressure
  6. customto give a residue
  7. customPurify the residue by silica gel chromatography
  8. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-c1325667372f4537a50927eda41f2e98
Source dataset
uspto-grants-2015_02
Patent number
US08962654B2

Reaction notes

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