Tetrabutylammonium Fluoride → HCID 10425446, compound

HRID 1196913Notes

Reaction equation

HRID 1196913 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]([C:17]2[CH:22]=[CH:21][C:20]([O:23][Si](C(C)(C)C)(C)C)=[CH:19][CH:18]=2)=[O:16])[CH2:10][CH2:9]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]1[CH2:9][CH2:10][CH:11]([CH2:14][C:15]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)=[O:16])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 10002430HCID 10002430, compound

Product 1

HCID 10425446HCID 10425446, compoundYield 26.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-benzyl-4-(2'-(4''-t-butyldimethylsilyloxyphenyl)-2'-oxoethyl)piperidine (Example 75, 1.21 g, 2.86 mmol), a solution of tetra-n-butylammonium fluoride (1.0 M in tetrahydrofuran, 5.7 mL, 5.7 mmol) and tetrahydrofuran (10 mL) were stirred at ambient temperature under a nitrogen atmosphere overnight. The reaction mixture was poured onto water and extracted three times with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was triturated with ethyl acetate and filtered. Drying in vacuo gave the title compound (238 mg): mp 197°-198° C.; 1H-NMR (CDCl3, 300 MHz): 7.8(d,2H,J=8), 7.4-6.8(m,7H), 3.5(s,2H), 3.2-3.0(br s,4H), 3.0-2.8(dd,4H,J=10,7), 2.5(s,1H), 2.1-1.2(m,4H); Anal.:Calcd for C20H23NO2 ·0.25H2O: C,76.53, H,7.55, N, 4.40; Found: C,76.63,76.54, H,7.47,7.31, N,4.23,4.26.

Workup

  1. additionThe reaction mixture was poured onto water
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with ethyl acetate
  7. filtrationfiltered
  8. customDrying in vacuo

Sources & evidence

ORD record
ord-d446c0919a9c457cbe602ccc8efbfc46
Source dataset
uspto-grants-1992_05
Patent number
US05116846

Reaction notes

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