Hydrochloric Acid → tert-Butyl 3-(trifluoroacetyl)piperidine-1-carboxylate

HRID 2355401Notes

Reaction equation

HRID 2355401 reaction equation
[N:1]1([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][CH2:5][CH2:4][CH:3]([C:7]([O:9]CC)=O)[CH2:2]1.[F-].[Cs+].N#N.[Si]([C:27]([F:30])([F:29])[F:28])(C)(C)C.Cl>C1COCC1>[F:28][C:27]([F:30])([F:29])[C:7]([CH:3]1[CH2:4][CH2:5][CH2:6][N:1]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[CH2:2]1)=[O:9]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 25953Cesium fluorideHCID 3577271-Tert-butyl 3-ethyl piperidine-1,3-dicarboxylateHCID 552549(Trifluoromethyl)trimethylsilane

Product 1

HCID 49759206tert-Butyl 3-(trifluoroacetyl)piperidine-1-carboxylateYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-tert-butyl 3-ethyl piperidine-1,3-dicarboxylate (424 mg, 1.65 mmol) and CsF (ca 10 mg) were combined in a vial under N2. Dry THF (3 mL) was added, followed by Me3SiCF3 (256 μL, 1.05 equiv). After stirring for 3 h, 4N aq HCl (4 mL) was added to the vial and the mixture was stirred for 1 h. The mixture was extracted with diethyl ether (2×15 mL). The combined organic layers were washed with brine (8 mL), dried over Na2SO4, and concentrated to afford tert-butyl 3-(2,2,2-trifluoroacetyl)piperidine-1-carboxylate (173 mg. 37%)

Workup

  1. stirringwas stirred for 1 h
  2. extractionThe mixture was extracted with diethyl ether (2×15 mL)
  3. washThe combined organic layers were washed with brine (8 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5e71426a006e46fbbf572b7abea002ea
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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