Triethylamine → HCID 66732094, compound

HRID 1963304Notes

Reaction equation

HRID 1963304 reaction equation
[CH3:1][S:2]([C:5]1[CH:25]=[CH:24][C:8]([CH2:9][CH:10]2[CH2:15][CH:14]([C:16]([O:18]C)=[O:17])[CH2:13][CH2:12][N:11]2[C:20]([O:22][CH3:23])=[O:21])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[Br-].[Li+].C(N(CC)CC)C.CC(OC)(C)C>C(#N)C.O>[CH3:23][O:22][C:20]([N:11]1[CH2:12][CH2:13][CH:14]([C:16]([OH:18])=[O:17])[CH2:15][CH:10]1[CH2:9][C:8]1[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:25][CH:24]=1)=[O:21]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 15413tert-Butyl methyl etherHCID 82050Lithium BromideHCID 66734526HCID 66734526, compound

Product 1

HCID 66732094HCID 66732094, compoundYield 79.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

Dimethyl 2-(4-(methylsulfonyl)benzyl)piperidine-1,4-dicarboxylate (5.5 g, 14.89 mmol) was dissolved in acetonitrile (50 mL) and water (1 mL), then lithium bromide (10.34 g, 119.10 mmol) and triethylamine (8.25 mL, 59.55 mmol) were added and the resulting suspension was heated at reflux for 2 h. Water and MTBE were added. The organic phase was extracted with water (×2). To the pooled aqueous layer was added ethyl acetate and the solution was acidified to pH 1 with HCl and then extracted with ethyl acetate twice. The organic layer was dried (Na2SO4), filtered through celite and evaporated to yield 1-(methoxycarbonyl)-2-(4-(methylsulfonyl)benzyl)piperidine-4-carboxylic acid (4.2 g, 79%). MS m/z 354 (M−H)−

Workup

  1. temperaturethe resulting suspension was heated
  2. temperatureat reflux for 2 h
  3. extractionThe organic phase was extracted with water (×2)
  4. additionTo the pooled aqueous layer was added ethyl acetate
  5. extractionextracted with ethyl acetate twice
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. filtrationfiltered through celite
  8. customevaporated

Sources & evidence

ORD record
ord-b8f5b188732c40b89ab3088423af9307
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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