Hydrochloric Acid → methyl(2R,6S)-6-(3,4-difluorophenyl)piperidine-2-carboxylate

HRID 1436124Notes

Reaction equation

HRID 1436124 reaction equation
Cl.C(OC([NH:9][C@H:10]([CH2:15][CH2:16][CH2:17][C:18]([C:20]1[CH:25]=[CH:24][C:23]([F:26])=[C:22]([F:27])[CH:21]=1)=O)[C:11]([O:13][CH3:14])=[O:12])=O)(C)(C)C>C(OCC)(=O)C>[F:27][C:22]1[CH:21]=[C:20]([C@H:18]2[NH:9][C@@H:10]([C:11]([O:13][CH3:14])=[O:12])[CH2:15][CH2:16][CH2:17]2)[CH:25]=[CH:24][C:23]=1[F:26]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67461441methyl(R)-2-tert-butoxycarbonylamino-6-(3,4-difluorophenyl)-6-oxohexanoate

Product 1

HCID 67463892methyl(2R,6S)-6-(3,4-difluorophenyl)piperidine-2-carboxylateYield 80.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 4 N hydrochloric acid in ethyl acetate (20 mL) was added to a solution of methyl(R)-2-tert-butoxycarbonylamino-6-(3,4-difluorophenyl)-6-oxohexanoate (3.8 g) in ethyl acetate (20 mL), and the reaction solution was stirred at room temperature for 5.5 hours. The reaction solution was concentrated under reduced pressure. Then, ethyl acetate and saturated sodium bicarbonate water were added to the residue, and the organic layer was separated. The resulting organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. 10% palladium-carbon (50 mg) was added to a solution of the resulting residue in methanol (20 mL), and the reaction solution was stirred in a hydrogen stream at room temperature for two hours. The reaction solution was filtered through celite, and the filtrate was concentrated under reduced pressure to obtain 2.1 g of the title compound. The property value of the compound is as follows.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionThen, ethyl acetate and saturated sodium bicarbonate water were added to the residue
  3. customthe organic layer was separated
  4. dry with materialThe resulting organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. addition10% palladium-carbon (50 mg) was added to a solution of the resulting residue in methanol (20 mL)
  7. stirringthe reaction solution was stirred in a hydrogen stream at room temperature for two hours
  8. filtrationThe reaction solution was filtered through celite
  9. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-abb7b7b205c04c17833982ce949cdbc2
Source dataset
uspto-grants-2009_11
Patent number
US07618960B2

Reaction notes

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