HCID 69841045, compound → HCID 89650227, compound

HRID 1479028Notes

Reaction equation

HRID 1479028 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[CH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]([O:23][CH3:24])=[O:22])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.C1COCC1.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]([O:23][CH3:24])=[O:22])[CH2:10][CH2:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 1

HCID 69841045HCID 69841045, compound

Product 1

HCID 89650227HCID 89650227, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-(2-methoxycarbonyl-benzylidene)-piperidine-1-carboxylic acid tert-butyl ester (from Intermediate B11 step 1) (350 mg; 1.06 mmol; 1 eq.) and 10% Pd/C (˜50% H2O) (67 mg) in MeOH (2 mL) and THF (2 mL) was stirred at room temperature for 3 hours under a H2 atmosphere (10 bars). The catalyst was filtered off and the solution concentrated in vacuo. Purification by column chromatography (heptane/EA) afforded the title compound (330 mg, 94%) as a colourless oil. HPLC (max plot) 97.4%; Rt 5.20 min.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe solution concentrated in vacuo
  3. customPurification by column chromatography (heptane/EA)

Sources & evidence

ORD record
ord-bcdfee64fa774386bd4f7ed9e6447fce
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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