Acetic Acid → HCID 21184169, compound

HRID 1384989Notes

Reaction equation

HRID 1384989 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-butyldimethylsilyloxy)-2,6-dimethylphenoxymethyl]-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 vacuo. 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 vacuo
  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-43463ad2e2e049e99b5eec54bb6407f8
Source dataset
uspto-grants-2001_07
Patent number
US06262078B1

Reaction notes

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