HCID 58494011, compound → HCID 58494099, compound

HRID 1942703Notes

Reaction equation

HRID 1942703 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][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[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][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:23][CH2:24]1)[CH3:2]

Participants

4

Reactant 1

HCID 58494011HCID 58494011, compound

Product 1

HCID 58494099HCID 58494099, compoundYield 88.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of ethyl 3-(4-{[2-ethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methylidene}-1-piperidinyl)propanoate (D139) (1.5 g, 3.51 mmol) in Ethanol (10 mL) was added Pd/C (0.037 g, 0.351 mmol). The reaction mixture was stirred under hydrogen atmosphere overnight. After filtration, the filtrate was concentrated to afford ethyl 3-(4-{[2-ethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}-1-piperidinyl)propanoate (D140) (1.33 g), which was used directly without further purification. MS (ES): C25H40BNO4 requires 429.3. found 430.2 (M+H+).

Workup

  1. filtrationAfter filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-6c3f1d7509784e9f8178b863b029e8d9
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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