1,4-Cyclohexadiene → HCID 67388645, compound

HRID 245142Notes

Reaction equation

HRID 245142 reaction equation
[OH:1][C@H:2]1[CH2:6][CH2:5][N:4]([CH:7]2[CH2:12][CH2:11][N:10](C(OCC3C=CC=CC=3)=O)[CH2:9][CH2:8]2)[CH2:3]1.C1CC=CCC=1>CO.[Pd]>[NH:10]1[CH2:11][CH2:12][CH:7]([N:4]2[CH2:5][CH2:6][C@H:2]([OH:1])[CH2:3]2)[CH2:8][CH2:9]1

Participants

5

Reactant 2

HCID 123431,4-CyclohexadieneHCID 67418881HCID 67418881, compound

Product 1

HCID 67388645HCID 67388645, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

Phenylmethyl 4-[(3S)-3-hydroxy-1-pyrrolidinyl]-1-piperidinecarboxylate (1.33 g, 4.37 mmol) was dissolved in methanol (11.65 ml) and 1,4-cyclohexadiene (2.91 ml) was added. The mixture was flushed with nitrogen and palladium on carbon (10%) (0.023 g, 0.218 mmol) was added. The reaction mixture was heated in an 80° C. oil bath at reflux for 1 h. The mixture was filtered through Celite®, washed with MeOH, and the filtrate was concentrated to afford (3S)-1-(4-piperidinyl)-3-pyrrolidinol (0.670 g, 81% yield). MS (m/z) 171.0 (M+H+).

Workup

  1. additionwas added
  2. temperatureat reflux for 1 h
  3. filtrationThe mixture was filtered through Celite®
  4. washwashed with MeOH
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a1dd862f4e514cae8a9ec60ffc1e019b
Source dataset
uspto-grants-2014_02
Patent number
US08658636B2

Reaction notes

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