Piperidin-4-ol → HCID 86730059, compound

HRID 1504602Notes

Reaction equation

HRID 1504602 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13](Cl)=[N:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH:17]1[CH2:22][CH2:21][CH:20]([OH:23])[CH2:19][CH2:18]1.CC([O-])(C)C.[K+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([N:17]2[CH2:22][CH2:21][CH:20]([OH:23])[CH2:19][CH2:18]2)=[N:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 79341Piperidin-4-olHCID 23665647Potassium tert-butoxideHCID 86730058HCID 86730058, compound

Product 1

HCID 86730059HCID 86730059, compoundYield 76.9%

Reagents, catalysts & solvents 3

HCID 634876Binap, (A+-)-CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 5-((tert-butyldimethylsilyloxy)methyl)-2-chloropyridine (650 mg, 2.5 mmol) in toluene (20 mL) was degassed with argon for 5 min, followed by adding piperidin-4-ol (303 mg, 3 mmol), t-BuOK (426 mg, 3.8 mmol), Pd2(dba)3 (23 mg, 0.0025 mmol) and BINAP (31 mg, 0.05 mmol). The resulting mixture was stirred at 90□ overnight under argon atmosphere. After cooling to rt, solid was removed by filtration and the filtrate was concentrated to dryness. The residue was dissolved in EtOAc (50 mL) and the mixture was washed with brine (50 mL), dried and concentrated to yield the desired product as dark oil (620 mg, 76%). [LCMS: RtA=1.59 min, m/z 323.2 [M+H]+].

Workup

  1. customwas degassed with argon for 5 min
  2. customsolid was removed by filtration
  3. concentrationthe filtrate was concentrated to dryness
  4. dissolutionThe residue was dissolved in EtOAc (50 mL)
  5. washthe mixture was washed with brine (50 mL)
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a54123f4e3254d9a8bd0904284a8f47e
Source dataset
uspto-grants-2015_12
Patent number
US09216182B2

Reaction notes

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