Tetrahydrofuran → HCID 67371748, compound

HRID 1677086Notes

Reaction equation

HRID 1677086 reaction equation
O1CCCC1.C[O:7][C:8]([C@H:10]1[CH2:15][CH2:14][CH2:13][C@@H:12]([C:16]2[CH:21]=[C:20]([F:22])[C:19]([F:23])=[C:18]([F:24])[CH:17]=2)[NH:11]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C(OCC)(=O)C.O>[F:22][C:20]1[CH:21]=[C:16]([C@H:12]2[NH:11][C@@H:10]([CH2:8][OH:7])[CH2:15][CH2:14][CH2:13]2)[CH:17]=[C:18]([F:24])[C:19]=1[F:23]

Participants

7

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 67372196methyl (2R,6S)-6-(3,4,5-trifluorophenyl)piperidine-2-carboxylate

Product 1

HCID 67371748HCID 67371748, compoundYield 98.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Under a nitrogen atmosphere, a tetrahydrofuran (10 mL) solution of (2R,6S)-6-(3,4,5-trifluorophenyl)piperidine-2-carboxylic acid methyl ester (3.25 g) was added dropwise at −20° C. into a tetrahydrofuran (50 mL) suspension of lithium aluminum hydride (621 mg). After confirming the disappearance of the raw materials, water (0.62 mL), 5 N sodium hydroxide solution (0.62 mL), and water (1.86 mL) were added in sequence to the reaction solution at the same temperature. After stirring for 15 minutes at the same temperature, ethyl acetate was added, and the resultant was filtered on celite. The filtrate was passed through a silica pad (carrier: Chromatrex NH, eluting solvent: ethyl acetate), and by removing the solvent under a vacuum, the title compound (2.87 g) was obtained. The physical property values are as follows.

Workup

  1. additionwere added in sequence to the reaction solution at the same temperature
  2. additionwas added
  3. filtrationthe resultant was filtered on celite
  4. washThe filtrate was passed through a silica pad (carrier: Chromatrex NH, eluting solvent: ethyl acetate)
  5. customby removing the solvent under a vacuum

Sources & evidence

ORD record
ord-cc05be737a0148189c265a275420dbea
Source dataset
uspto-grants-2011_08
Patent number
US08008293B2

Reaction notes

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