Triethylamine → 1'-Benzyl-1H-spiro[furo[3,4-c]pyridine-3,4'-piperidine]

HRID 1663339Notes

Reaction equation

HRID 1663339 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([OH:22])([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][C:19]=2[CH2:20]O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.CS(Cl)(=O)=O>O1CCCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][C:19]=3[CH2:20][O:22]2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 597568131'-Benzyl-4-hydroxymethyl-2',3',5',6'-tetrahydro-1'H-[3,4']bipyridinyl-4'-ol

Product 1

HCID 597568161'-Benzyl-1H-spiro[furo[3,4-c]pyridine-3,4'-piperidine]Yield 123.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.46 g (1.5 mmol) 1′-benzyl-4-hydroxymethyl-2′,3′,5′,6′-tetrahydro-1′H-[3,4′]bipyridinyl-4′-ol and 0.45 ml (3.2 mmol) triethylamine in 15 ml dry tetrahydrofuran at were added 0.11 ml (1.5 mmol) methane sulfonyl chloride room temperature. The reaction mixture was heated at reflux for 1 h and then quenched with water. The aqueous layer was basified with aqueous 1 M sodium hydroxide and extracted with three portions of ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated in vacuo. Flash-chromatography (aminopropyl-modified silica gel) gave the title compound (0.52 g, 57%) as a light yellow amorphous solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 1 h
  3. customquenched with water
  4. extractionextracted with three portions of ethyl acetate
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9a442d66ee2e42638b709309b11383e3
Source dataset
uspto-grants-2011_10
Patent number
US08034937B2

Reaction notes

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