tert-Butyl 4-(7-fluorobenzofuran-2-yl)piperidine-1-carboxylate → tert-Butyl 4-(7-fluoro-2,3-dihydrobenzofuran-2-yl)piperidine-1-carboxylate

HRID 1025496Notes

Reaction equation

HRID 1025496 reaction equation
[F:1][C:2]1[C:10]2[O:9][C:8]([CH:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)=[CH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1>CCO.[Pd]>[F:1][C:2]1[C:10]2[O:9][CH:8]([CH:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)[CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 68211765tert-Butyl 4-(7-fluorobenzofuran-2-yl)piperidine-1-carboxylate

Product 1

HCID 67467702tert-Butyl 4-(7-fluoro-2,3-dihydrobenzofuran-2-yl)piperidine-1-carboxylateYield 87.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a degassed solution of tert-butyl 4-(7-fluorobenzofuran-2-yl)piperidine-1-carboxylate (3.4 g, 8.41 mmol) in EtOH (54.3 mL) was added 10% Pd—C (2.69 g, 2.52 mmol). Upon completion of addition, the reaction mixture was charged with 55 psi of H2 overnight. At the conclusion of this period, the Pd—C was filtered off through a pad of CELITE®, and the filter cake was rinsed with EtOH. The filtrate was concentrated under reduced pressure to afford Compound 3C as a colorless oil (2.36 g, 87% yield), which was used in next step without further purification. LC/MS (m/z)=344 (M+Na)+.

Workup

  1. additionUpon completion of addition
  2. additionthe reaction mixture was charged with 55 psi of H2 overnight
  3. filtrationAt the conclusion of this period, the Pd—C was filtered off through a pad of CELITE®
  4. washthe filter cake was rinsed with EtOH
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9cf0c1a04fa8436fa36426a55c4a40f3
Source dataset
uspto-grants-2014_05
Patent number
US08729084B2

Reaction notes

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