HCID 57496381, compound → HCID 57496382, compound

HRID 537735Notes

Reaction equation

HRID 537735 reaction equation
[CH:1]1([CH:7]2[CH2:12][C:11](=[O:13])[CH2:10][CH2:9][N:8]2[C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:24]1([Mg]Br)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1COCC1>[CH:1]1([CH:7]2[CH2:12][C:11]([OH:13])([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:10][CH2:9][N:8]2[C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 57496381HCID 57496381, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 57496382HCID 57496382, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzyl 2-cyclohexyl-4-oxopiperidine-1-carboxylate in THF (155 ml) was cooled to 0° C. and added phenylmagnesium bromide (22.08 ml, 61.8 mmol). The ice bath was removed and the solution stirred at room temperature for 14 hours. Quenched the reaction with 1N HCl and concentrated. Extracted three times with EtOAc and washed twice with water. The organics were dried, concentrated, and purified on silica gel 30% EtOAc.

Workup

  1. customThe ice bath was removed
  2. customQuenched
  3. customthe reaction with 1N HCl
  4. concentrationconcentrated
  5. extractionExtracted three times with EtOAc
  6. washwashed twice with water
  7. customThe organics were dried
  8. concentrationconcentrated
  9. custompurified on silica gel 30% EtOAc

Sources & evidence

ORD record
ord-81a6ffb47ac84a529d2f2337f232c91c
Source dataset
uspto-grants-2014_10
Patent number
US08865701B2

Reaction notes

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