Acetic Acid → HCID 21184169, compound

HRID 1872679Notes

Reaction equation

HRID 1872679 reaction equation
[Si]([O:8][C:9]1[CH:23]=[C:22]([CH3:24])[C:12]([O:13][CH2:14][CH:15]2[CH2:20][CH2:19][CH2:18][N:17]([CH3:21])[CH2:16]2)=[C:11]([CH3:25])[CH:10]=1)(C(C)(C)C)(C)C.C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:8][C:9]1[CH:23]=[C:22]([CH3:24])[C:12]([O:13][CH2:14][CH:15]2[CH2:20][CH2:19][CH2:18][N:17]([CH3:21])[CH2:16]2)=[C:11]([CH3:25])[CH:10]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 21184155HCID 21184155, compound

Product 1

HCID 21184169HCID 21184169, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-[4-(tert-butyidimethylsilyloxy)-2,6dimethylphenoxymethyl]-1-methylpiperidine (3.2 g, 8.8 mmol) in tetrahydrofuran (50 mL) containing 20% acetic acid (5.5 mL, 19 mmol) at 0° C. was added 1M tetrabutylammonium fluoride in tetrahydrofuran (17.5 mL). The mixture was stirred from 0° C. to room temperature overnight and concentrated in vacua. The residue was partitioned between water and dichloromethane. The organic layer was dried and concentrated and the residue purified on silica gel, eluting with 5% methanol in dichloromethane containing 0.25% ammonium hydroxide, to give 3-(4-hydroxy-2,6-dimethylphenoxymethyl)-1 -methylpiperidine.

Workup

  1. concentrationconcentrated in vacua
  2. customThe residue was partitioned between water and dichloromethane
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customthe residue purified on silica gel
  6. washeluting with 5% methanol in dichloromethane containing 0.25% ammonium hydroxide

Sources & evidence

ORD record
ord-699faf203367464799207ecc3682a5cd
Source dataset
uspto-grants-2000_08
Patent number
US06110937

Reaction notes

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