Tetrabutylammonium Fluoride → HCID 66817261, compound

HRID 1755004Notes

Reaction equation

HRID 1755004 reaction equation
[F-:1].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]([O:23][C:24]([N:26]1[CH2:33][CH2:32][C:29]2([O:31][CH2:30]2)[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]>O1CCCC1>[C:19]([O:23][C:24]([N:26]1[CH2:33][CH2:32][C:29]([CH2:30][F:1])([OH:31])[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 22135564tert-Butyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylate

Product 1

HCID 66817261HCID 66817261, compoundYield 19.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride (1.0 M in THF, 5.6 ml, 5.6 mmol) was added to a solution of 1-oxa-6-aza-spiro[2.5]octane-6-carboxylic acid tert-butyl ester (400 mg, 1.87 mmol) in tetrahydrofuran (5 ml), and the mixture was heated under reflux for 36 hours. The reaction solution was cooled and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate-hexane) to give 4-fluoromethyl-4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (87 mg, 19%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 36 hours
  3. temperatureThe reaction solution was cooled
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-06cf47aeade94fddbd7dbc01210a86d0
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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