Ethyl (4-{[2-ethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methylidene}-1-piperidinyl)acetate → HCID 58494160, compound

HRID 1942706Notes

Reaction equation

HRID 1942706 reaction equation
[CH2:1]([C:3]1[C:8]([B:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]2)=[CH:7][CH:6]=[CH:5][C:4]=1[CH:18]=[C:19]1[CH2:24][CH2:23][N:22]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:21][CH2:20]1)[CH3:2]>C(O)C.[Pd]>[CH2:1]([C:3]1[C:8]([B:9]2[O:13][C:12]([CH3:14])([CH3:15])[C:11]([CH3:17])([CH3:16])[O:10]2)=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:18][CH:19]1[CH2:20][CH2:21][N:22]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:23][CH2:24]1)[CH3:2]

Participants

4

Reactant 1

HCID 58494165Ethyl (4-{[2-ethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methylidene}-1-piperidinyl)acetate

Product 1

HCID 58494160HCID 58494160, compoundYield 80.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of ethyl (4-{[2-ethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methylidene}-1-piperidinyl)acetate (D143) (0.37 g, 0.895 mmol) in Ethanol (10 mL) was added Pd/C (0.191 g, 0.179 mmol). The reaction solution was stirred under hydrogen atmosphere for 4 hours. After filtration, the filtrate was concentrated to afford ethyl (4-{[2-ethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}-1-piperidinyl)acetate (D144) (300 mg). MS (ES): C24H38BNO4 requires 415.3. found 416.3 (M+H+).

Workup

  1. filtrationAfter filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e00b265b43cd457ca56f0f3790ada986
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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