Boron trifluoride → 644982-11-6

HRID 2035581Notes

Reaction equation

HRID 2035581 reaction equation
[F:1][CH:2]1[C:7](=[O:8])[CH2:6][CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]1.B(F)(F)F.[N+](=[CH:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[N-].O=C1CCCCN1>O.CCOCC.C(Cl)Cl>[F:1][CH:2]1[CH2:3][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:6][CH:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:7]1=[O:8]

Participants

8

Reactant 4

HCID 6356Boron trifluorideHCID 12192Ethyl diazoacetateHCID 126652-PiperidoneHCID 10560711TERT-BUTYL 3-FLUORO-4-OXOPIPERIDINE-1-CARBOXYLATE

Product 1

HCID 67230662644982-11-6Yield 93.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of tert-butyl 3-fluoro-4-oxopiperidine-1-carboxylate (20.0 g, 92.1 mmol) in 1:1 (CH2Cl2:Et2O, 250 mL) was cooled to −60° C. using an IPA/dry ice bath. In a separate flask was added BF3-Etherate (12.8 mL, 101 mmol) and Et2O (40 mL) which was cooled to 0° C., then ethyl 2-diazoacetate (12.6 mL, 120 mmol) was added. This mixture was added to the oxopiperidine solution and the reaction mixture was slowly warmed to ambient temperature over 2 hours. Water was added (100 mL) and the mixture was stirred at ambient temperature for 30 minutes. The phases were separated and the aqueous phase was extracted with EtOAc (100 mL) and the combined organic phases were washed with 1N KHSO4, followed by brine and then dried over Na2SO4, filtered and concentrated. This provided the product as a thick, yellow oil (26 g).

Workup

  1. temperaturethe reaction mixture was slowly warmed to ambient temperature over 2 hours
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with EtOAc (100 mL)
  4. washthe combined organic phases were washed with 1N KHSO4
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-69437170261f47c288d48057b5b9a043
Source dataset
uspto-grants-2013_11
Patent number
US08575145B2

Reaction notes

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