Tetrabutylammonium Fluoride → HCID 24824075, compound

HRID 1866185Notes

Reaction equation

HRID 1866185 reaction equation
[CH2:1]([N:8]([CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([CH:34]([C:36]2[CH:41]=[CH:40][C:39]([O:42][Si](C(C)(C)C)(C)C)=[CH:38][CH:37]=2)[OH:35])=[CH:30][CH:29]=1)[CH2:9][C@H:10]([O:18][Si](C(C)(C)C)(C)C)[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:1]([N:8]([CH2:26][CH2:27][C:28]1[CH:29]=[CH:30][C:31]([CH:34]([OH:35])[C:36]2[CH:37]=[CH:38][C:39]([OH:42])=[CH:40][CH:41]=2)=[CH:32][CH:33]=1)[CH2:9][C@@H:10]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=1)[OH:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 24823941HCID 24823941, compound

Product 1

HCID 24824075HCID 24824075, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of [4-[2-[N-benzyl-N-[(2R)-2-[[tert-butyl(dimethyl)silyl]oxy]-2-(3-chlorophenyl)ethyl]amino]-ethyl]phenyl][4-[[tert-butyl(dimethyl)silyl]oxy]phenyl]-methanol (1.1 g) in tetrahydrofuran (15 ml) was added 1M tetrabutylammonium fluoride in tetrahydrofuran (5.0 ml) at 0° C., and the mixture was stirred at room temperature for 24 hours under nitrogen. The mixture was partitioned between ethyl acetate and water. The organic layer was separated, washed with water and brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=2/1) to give 4-[[4-[2-[N-benzyl-N-[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethyl]-phenyl](hydroxy)methyl]phenol (550 mg).

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-de8d36bbe2bc4d6fbd154891eb0f7b0d
Source dataset
uspto-grants-2009_12
Patent number
US07629366B2

Reaction notes

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