Triethylamine → 1'-Benzyl-5H-spiro[furo[3,4-b]pyridine-7,4'-piperidine]

HRID 1666958Notes

Reaction equation

HRID 1666958 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([OH:22])([C:14]2[C:19]([CH2:20]O)=[CH:18][CH:17]=[CH:16][N:15]=2)[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[CH2:9][CH2:10][C:11]2([C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:19]3[CH2:20][O:22]2)[CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 597568262-[4-Hydroxy-1-(phenylmethyl)-4-piperidinyl]-3-pyridinemethanol

Product 1

HCID 597568191'-Benzyl-5H-spiro[furo[3,4-b]pyridine-7,4'-piperidine]Yield 63.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.1 g (3.5 mmol) 1′-benzyl-3-hydroxymethyl-2′,3′,5′,6′-tetrahydro-1′H-[2,4′]bipyridinyl-4′-ol and 1.0 ml (7.4 mmol) triethylamine in 35 ml dry tetrahydrofuran were added 0.26 ml (3.3 mmol) methane sulfonyl chloride at 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 (0.62 g, 62%) 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-eb1e269dd3c04ac19333bdc66195eb5f
Source dataset
uspto-grants-2011_10
Patent number
US08044202B2

Reaction notes

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