[3-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)-2-ethylphenyl]boronic Acid Pinacol Ester → HCID 58494122, compound

HRID 1942684Notes

Reaction equation

HRID 1942684 reaction equation
C([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([B:20]3[O:24][C:23]([CH3:26])([CH3:25])[C:22]([CH3:28])([CH3:27])[O:21]3)[C:15]=2[CH2:29][CH3:30])[CH2:10][CH2:9]1)C1C=CC=CC=1>CCOC(C)=O.[Pd]>[CH2:29]([C:15]1[C:16]([B:20]2[O:21][C:22]([CH3:27])([CH3:28])[C:23]([CH3:26])([CH3:25])[O:24]2)=[CH:17][CH:18]=[CH:19][C:14]=1[CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)[CH3:30]

Participants

4

Reactant 1

HCID 58494102[3-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)-2-ethylphenyl]boronic Acid Pinacol Ester

Product 1

HCID 58494122HCID 58494122, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-benzyl-4-[2-ethyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1,2,3,6-tetrahydro-pyridine (D118) (8 g, 19.83 mmol) in EtOAc (300 mL) was added dry Pd/C (8 g, 10%). The reaction mixture was hydrogenated under 55 psi at 50° C. for 12 hr, and then filtered. The filtrate was concentrated in vacuo. The residue was purified by Mass Directed AutoPrep to give 4-[2-Ethyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-piperidine (D119) (2.5 g). MS (ES): C19H30BNO2 requires 315.2. found 316.2 (M+H+).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customThe residue was purified by Mass Directed AutoPrep

Sources & evidence

ORD record
ord-f8724074610c447f80e633b90719c36a
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

Loading…