Triethylamine → HCID 66731923, compound

HRID 1963343Notes

Reaction equation

HRID 1963343 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:23]=[C:24]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:25]=1)[CH2:8][CH:9]1[CH2:14][CH:13]([C:15]([O:17]C)=[O:16])[CH2:12][CH2:11][N:10]1[C:19]([O:21][CH3:22])=[O:20])([CH3:4])([CH3:3])[CH3:2].[Br-].[Li+].C(N(CC)CC)C.CC(OC)(C)C>C(#N)C.O>[C:1]([C:5]1[CH:6]=[C:7]([CH:23]=[C:24]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:25]=1)[CH2:8][CH:9]1[CH2:14][CH:13]([C:15]([OH:17])=[O:16])[CH2:12][CH2:11][N:10]1[C:19]([O:21][CH3:22])=[O:20])([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 15413tert-Butyl methyl etherHCID 82050Lithium BromideHCID 66734972HCID 66734972, compound

Product 1

HCID 66731923HCID 66731923, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

Dimethyl 2-(3,5-di-tert-butylbenzyl)piperidine-1,4-dicarboxylate (3.886 g, 9.63 mmol) was dissolved in acetonitrile (40 mL) and water (0.8 mL), then lithium bromide (6.69 g, 77.04 mmol) and triethylamine (5.34 mL, 38.52 mmol) were added and the resulting yellow suspension was heated at reflux. After 5 h water (100 mL) and MTBE (250 mL) were added. The organic phase was extracted with water (×2). The pooled aqueous layer was acidified to pH 1 with 3.8 M HCl and then extracted with MTBE (×3). The combined organic layer was washed with water, dried Na2SO4, filtered and evaporated to yield 2-(3,5-di-tert-butylbenzyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acid (3.723 g, 99%) as a yellow gum. MS m/z 390 (M+H)+

Workup

  1. temperaturethe resulting yellow suspension was heated
  2. temperatureat reflux
  3. extractionThe organic phase was extracted with water (×2)
  4. extractionextracted with MTBE (×3)
  5. washThe combined organic layer was washed with water, dried Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-4c00457fb97e46098fc8be50f44d8c6e
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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