2-Methyl-6-(3-piperidin-4-ylideneprop-1-ynyl)pyridine → 2-(Piperidin-4-yl)but-3-yn-2-ol

Reaction equation

CC1C=CC=C(C#CC=C2CCNCC2)N=1.[OH:17][C:18]([CH:22]1[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]1)([CH3:21])[C:19]#[CH:20]>>[NH:25]1[CH2:26][CH2:27][CH:22]([C:18]([OH:17])([C:19]#[CH:20])[CH3:21])[CH2:23][CH2:24]1

Participants

Reactant 2

HCID 875504022-Methyl-6-(3-piperidin-4-ylideneprop-1-ynyl)pyridine

HCID 87550972Tert-butyl 4-(1-hydroxy-1-methylprop-2-ynyl)piperidine-1-carboxylate

Product 1

HCID 866273582-(Piperidin-4-yl)but-3-yn-2-ol

Procedure

The title compounds were obtained following the procedure described for the compound of Example 3 and replacing the Compound of Example 2 with Compound 312a refluxing for 6 h. The crude was used without further purification in the next step.

Workup

temperaturerefluxing for 6 h
customThe crude was used without further purification in the next step

Sources & evidence

ORD record: ord-4027678fd64049a5810448a3d002f954
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08518916B2

Reaction notes

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