Triethylamine → HCID 57880560, compound

HRID 1816974Notes

Reaction equation

HRID 1816974 reaction equation
[C:1]([N:8]1[CH2:16][CH2:15][CH:11]([C:12]([OH:14])=O)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:17][C:18]1([CH3:26])[O:25][C:23](=[O:24])[CH2:22][C:20](=[O:21])[O:19]1.C(P(=O)(OCC)OCC)#N.C(N(CC)CC)C>CN(C=O)C>[CH3:17][C:18]1([CH3:26])[O:25][C:23](=[O:24])[C:22](=[C:12]([OH:14])[CH:11]2[CH2:10][CH2:9][N:8]([C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[CH2:16][CH2:15]2)[C:20](=[O:21])[O:19]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 76257Diethyl cyanophosphonateHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acid

Product 1

HCID 57880560HCID 57880560, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A cooled (0° C.) solution of Boc-isonipecotic acid (5.97 g, 26.0 mmol) and Meldrum's acid (3.75 g, 26.0 mmol) in DMF (54 mL) was treated dropwise with diethyl cyanophosphonate (4.34 mL, 28.6 mmol) and triethylamine (11.2 mL, 80.7 mmol). After stirring at 0° C. for an additional 30 min the reaction mixture was permitted to warm to rt and stir over 3 days. The reaction mixture was concentrated under reduced pressure and ether and 1N HCl solution were added. The aqueous layer was extracted again with ether and the ethereal layers were combined and washed with 1N HCl solution, twice with water, and lastly with brine. He ethereal layer was then dried over anhydrous MgSO4, filtered, and concentrated to give tert-butyl 4-[(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)(hydroxy)methyl]piperidine-1-carboxylate which contained approximately 10% of Boc-isonipecotic acid.

Workup

  1. temperatureto warm to rt
  2. stirringstir over 3 days
  3. concentrationThe reaction mixture was concentrated under reduced pressure and ether and 1N HCl solution
  4. additionwere added
  5. extractionThe aqueous layer was extracted again with ether
  6. washwashed with 1N HCl solution, twice with water
  7. dry with materialwas then dried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-bdfefeba3040430fbd5c3bae6a2456bc
Source dataset
uspto-grants-2009_10
Patent number
US07598243B2

Reaction notes

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