Hydrochloric Acid → HCID 67505669, compound

HRID 473793Notes

Reaction equation

HRID 473793 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[F:15][C:16]1[CH:17]=[C:18]([Mg]Br)[CH:19]=[C:20]([F:23])[C:21]=1[F:22].Cl>O1CCCC1>[O:1]=[C:2]([C:18]1[CH:17]=[C:16]([F:15])[C:21]([F:22])=[C:20]([F:23])[CH:19]=1)[CH2:7][CH2:6][CH2:5][CH2:4][NH:3][C:8](=[O:9])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7577838tert-Butyl 2-oxopiperidine-1-carboxylateHCID 178505944HCID 178505944, compound

Product 1

HCID 67505669HCID 67505669, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of tert-butyl 2-oxopiperidine-1-carboxylate (0.30 g, 1.51 mmol) in tetrahydrofuran (8 mL) cooled to −78° C. was added slowly over 15 minutes 0.3 M 3,4,5-trifluorophenylmagnesium bromide in tetrahydrofuran (3.30 mL, 1.66 mmol) and the mixture was then allowed to warm to 25° C. over 30 minutes. The reaction mixture was poured slowly into an ice cold solution of 0.5 N hydrochloric acid (100 mL), and extracted twice with ethyl acetate (2×50 mL). The combined organic extracts were dried over anhydrous sodium sulfate then filtered and concentrated. The residue was purified by silica gel column chromatography (diethyl ether/hexanes 1:4) to give tert-butyl 5-oxo-5-(3,4,5-trifluorophenyl)pentylcarbamate (0.18 g, 36% yield). MS (EI) for C16H20F3NO3: 332 (MH+).

Workup

  1. extractionextracted twice with ethyl acetate (2×50 mL)
  2. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  3. filtrationthen filtered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (diethyl ether/hexanes 1:4)

Sources & evidence

ORD record
ord-44817490716941cb95e3eb0315670b82
Source dataset
uspto-grants-2014_01
Patent number
US08637499B2

Reaction notes

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