Phenylacetylene → tert-Butyl 4-(1-Fluoro-3-phenylprop-2-ynylidene)piperidine-1-carboxylate

HRID 1895972Notes

Reaction equation

HRID 1895972 reaction equation
C(C1C=C(C#CC=C2CCN(C(OC(C)(C)C)=O)CC2)C=NC=1)#N.[C:25]1([C:31]#[CH:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=C1CCN(C(OC(C)(C)C)=O)CC1)C#C.Br[C:50]([F:64])=[C:51]1[CH2:56][CH2:55][N:54]([C:57]([O:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[O:58])[CH2:53][CH2:52]1>>[F:64][C:50](=[C:51]1[CH2:56][CH2:55][N:54]([C:57]([O:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[O:58])[CH2:53][CH2:52]1)[C:32]#[C:31][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 4

HCID 10821PhenylacetyleneHCID 25183829Tert-butyl 4-[3-(5-cyanopyridin-3-yl)prop-2-ynylidene]piperidine-1-carboxylateHCID 68795703Tert-butyl 4-[bromo(fluoro)methylidene]piperidine-1-carboxylateHCID 86661548tert-Butyl 4-(prop-2-yn-1-ylidene)piperidine-1-carboxylate

Product 1

HCID 86627338tert-Butyl 4-(1-Fluoro-3-phenylprop-2-ynylidene)piperidine-1-carboxylate

Procedure

The title product was prepared following the procedure reported for the Compound of Example 45 but using phenylacetylene instead of instead of Compound 2b and Compound 66a instead of 5-bromonicotinonitrile. The residue coming from the usual work-up procedure was purified by flash chromatography (EtOAc—Petroleum Ether gradient from 5:95 to 10:90).

Workup

  1. customwas purified by flash chromatography (EtOAc—Petroleum Ether gradient from 5:95 to 10:90)

Sources & evidence

ORD record
ord-251b94293d13405c9c9456a5730860d3
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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