1''-Cyano-5-(1-methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1'-cyclobutane-3',4''-piperidine] → 1''-(3-Isopropyl-[1,2,4]oxadiazol-5-yl)-5-(1-methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1'-cyclobutane-3',4''-piperidine]

HRID 2406357Notes

Reaction equation

HRID 2406357 reaction equation
[OH:1][NH:2][C:3](=[NH:7])[CH:4]([CH3:6])[CH3:5].[C:8]([N:10]1[CH2:15][CH2:14][C:13]2([CH2:18][C:17]3([O:36][C:21]4=[CH:22][N:23]=[C:24]([C:26]5[CH2:27][CH2:28][N:29]([S:32]([CH3:35])(=[O:34])=[O:33])[CH2:30][CH:31]=5)[CH:25]=[C:20]4[CH2:19]3)[CH2:16]2)[CH2:12][CH2:11]1)#N>O1CCCC1.C(OCC)(=O)C.[Cl-].[Zn+2].[Cl-]>[CH:4]([C:3]1[N:7]=[C:8]([N:10]2[CH2:11][CH2:12][C:13]3([CH2:18][C:17]4([O:36][C:21]5=[CH:22][N:23]=[C:24]([C:26]6[CH2:31][CH2:30][N:29]([S:32]([CH3:35])(=[O:33])=[O:34])[CH2:28][CH:27]=6)[CH:25]=[C:20]5[CH2:19]4)[CH2:16]3)[CH2:14][CH2:15]2)[O:1][N:2]=1)([CH3:6])[CH3:5]

Participants

6

Reactant 2

HCID 867012031''-Cyano-5-(1-methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1'-cyclobutane-3',4''-piperidine]HCID 178449908HCID 178449908, compound

Product 1

HCID 721949801''-(3-Isopropyl-[1,2,4]oxadiazol-5-yl)-5-(1-methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1'-cyclobutane-3',4''-piperidine]

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Zinc chloride (0.7 mol/L in tetrahydrofuran, 0.42 mL) is added to a solution of N-hydroxy-isobutyramidine (30 mg) and 1″-cyano-5-(1-methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1′-cyclobutane-3′,4″-piperidine] (100 mg) in tetrahydrofuran (4 mL) and ethyl acetate (4 mL) at room temperature. The solution is heated to 60° C. and stirred at this temperature for 2 h.

Sources & evidence

ORD record
ord-c2fb4b0c5e3f4020b99e13518561b7b9
Source dataset
uspto-grants-2014_08
Patent number
US08809361B2

Reaction notes

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