Ethyl Acetate → HCID 67047186, compound

HRID 914850Notes

Reaction equation

HRID 914850 reaction equation
C([N:8]1[CH2:13][CH2:12][C@H:11]([OH:14])[C@H:10]([CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[F:23])[CH2:9]1)C1C=CC=CC=1.C(OCC)(=O)C>C(O)C.[OH-].[Pd+2].[OH-].[C]>[F:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[O:16][CH2:15][C@H:10]1[C@@H:11]([OH:14])[CH2:12][CH2:13][NH:8][CH2:9]1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 67047620HCID 67047620, compound

Product 1

HCID 67047186HCID 67047186, compoundYield 96.1%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 702EthanolSolvent

Procedure

After dissolving 402 mg of cis-1-benzyl-3-(2-fluorophenoxymethyl)-4-hydroxypiperidine in 20 ml of ethanol, 0.2 g of 20% palladium hydroxide-carbon (hydrous) was added and the mixture was stirred at room temperature under a hydrogen atmosphere (1 atm). The mixture was further stirred for 5.5 hours, and then ethyl acetate was added thereto and the insoluble portion was filtered off. The filtrate was distilled off under reduced pressure to obtain the title compound (276 mg, 94% yield).

Workup

  1. additionwas added
  2. stirringThe mixture was further stirred for 5.5 hours
  3. filtrationthe insoluble portion was filtered off
  4. distillationThe filtrate was distilled off under reduced pressure

Sources & evidence

ORD record
ord-60528131772f44d3a8aa74cfaa928de1
Source dataset
uspto-grants-2007_09
Patent number
US07265108B2

Reaction notes

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