Tetrabutylammonium Fluoride → HCID 66817261, compound

HRID 473836Notes

Reaction equation

HRID 473836 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)[CH2:4]OS1(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC.[F-:37]>C1COCC1>[F:37][CH2:4][C:5]1([OH:1])[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 72208074HCID 72208074, compound

Product 1

HCID 66817261HCID 66817261, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

1,1-dimethylethyl 1,3-dioxa-2-thia-8-azaspiro[4.5]decane-8-carboxylate 2,2-dioxide (500 mg, 1.7 mmol) was taken into THF (5 mL) followed by addition of TBAF (1M in THF, 1.8 mL) and the resulting solution was stirred for 3 h at 40° C. The mixture was then cooled and partitioned with ethyl acetate and 20% aqueous citric acid. The organic solution was washed with brine then dried over anhydrous sodium sulfate, filtered and concentrated to afford tert-butyl 4-(fluoromethyl)-4-hydroxypiperidine-1-carboxylate (350 mg, 88% yield). GC-MS (EI) for C11H20FNO3: 233 (M+). BOC-group deprotection was carried out in a manner well established in the literature (see, Greene and Wuts, Protective Groups in Organic Synthesis, Wiley-Interscience) to give 4-(fluoromethyl)piperidin-4-ol hydrochloride salt as a colorless solid.

Workup

  1. temperatureThe mixture was then cooled
  2. custompartitioned with ethyl acetate and 20% aqueous citric acid
  3. washThe organic solution was washed with brine
  4. dry with materialthen dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-522ca1d631704752a68dc40e0939f475
Source dataset
uspto-grants-2014_01
Patent number
US08637499B2

Reaction notes

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