Water → HCID 67371748, compound

HRID 1436122Notes

Reaction equation

HRID 1436122 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]1[CH:9]=[C:10]([C@H:16]2[NH:21][C@@H:20]([C:22](OC)=[O:23])[CH2:19][CH2:18][CH2:17]2)[CH:11]=[C:12]([F:15])[C:13]=1[F:14].O.[OH-].[Na+]>C1COCC1>[F:15][C:12]1[CH:11]=[C:10]([C@H:16]2[NH:21][C@@H:20]([CH2:22][OH:23])[CH2:19][CH2:18][CH2:17]2)[CH:9]=[C:8]([F:7])[C:13]=1[F:14]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 67372196methyl (2R,6S)-6-(3,4,5-trifluorophenyl)piperidine-2-carboxylate

Product 1

HCID 67371748HCID 67371748, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

LAH (75 mg) was added in three portions to a solution of methyl(2R,6S)-6-(3,4,5-trifluorophenyl)piperidine-2-carboxylate (270 mg) in THF (5 mL) at −20° C. over 15 minutes. The reaction solution was stirred at −20° C. for one hour, and water (0.1 mL), a 5 N sodium hydroxide solution (0.1 mL), and water (0.3 mL) were sequentially added to the reaction solution. The mixture was heated to room temperature and filtered through celite. The filtrate was concentrated under reduced pressure to obtain 242 mg of the title compound. The property value of the compound is as follows.

Workup

  1. temperatureThe mixture was heated to room temperature
  2. filtrationfiltered through celite
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d655c5d48b754930a4b237930493c662
Source dataset
uspto-grants-2009_11
Patent number
US07618960B2

Reaction notes

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