5-(3,6-dihydro-2H-pyran-4-yl)pyridin-3-amine → 5-(tetrahydro-2H-pyran-4-yl)pyridin-3-amine

HRID 1431567Notes

Reaction equation

[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:8]=[C:9]([NH2:13])[CH:10]=[N:11][CH:12]=2)[CH2:3][CH2:2]1>CCOC(C)=O.CCO.[Pd]>[O:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:8]=[C:9]([NH2:13])[CH:10]=[N:11][CH:12]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 23 °C

Procedure

To a flask containing 5-(3,6-dihydro-2H-pyran-4-yl)pyridin-3-amine (61.6 mg, 0.35 mmol) in EtOAc (3.0 mL) and EtOH (1.0 mL) was added 10% palladium on activated carbon (75.7 mg, 0.071 mmol). After purging, the mixture was stirred under an atmosphere of hydrogen at 23° C. The reaction was monitored with TLC and LC-MS. After 19 h, the reaction was filtered through Celite™. After concentration, the residue was identified as 5-(tetrahydro-2H-pyran-4-yl)pyridin-3-amine that was used without purification. Mass Spectrum (pos.) m/e: 179.1 (M+1).

Workup

customAfter purging
filtrationthe reaction was filtered through Celite™
concentrationAfter concentration
customwas used without purification

Sources & evidence

ORD record: ord-e1bbf93e18454ed6bcfa61b46046579f
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940724B2

Reaction notes

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