Tributylphosphine → HCID 69038857, compound

HRID 736575Notes

Reaction equation

HRID 736575 reaction equation
[CH2:1]([P:5]([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].[Br:14][CH2:15][CH2:16][CH2:17][O:18][C:19](=[O:37])[CH:20]([O:22][N:23]1[C:28]([CH2:30][CH3:31])([CH3:29])[CH2:27][CH:26]([OH:32])[CH:25]([CH3:33])[C:24]1([CH2:35][CH3:36])[CH3:34])[CH3:21]>C(#N)C>[Br-:14].[CH2:10]([P+:5]([CH2:1][CH2:2][CH2:3][CH3:4])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:15][CH2:16][CH2:17][O:18][C:19](=[O:37])[CH:20]([O:22][N:23]1[C:28]([CH2:30][CH3:31])([CH3:29])[CH2:27][CH:26]([OH:32])[CH:25]([CH3:33])[C:24]1([CH2:35][CH3:36])[CH3:34])[CH3:21])[CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 13831TributylphosphineHCID 67290503HCID 67290503, compound

Product 1

HCID 69038857HCID 69038857, compoundYield 105.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

Tributylphosphine (3 ml, 0.012 mol) is added to a solution of 2-(2,6-diethyl-4-hydroxy-2,3,6-trimethyl-piperidine-1-yloxy)-propionic acid 3-bromo-propyl ester (4.08 g, 0.01 mol) in acetonitrile (5 ml). The solution is stirred under argon at 60° C. for 23 h. The solvent is evaporated and the residue is triturated with diethyl ether (2×15 ml) to remove the excess of the phosphine. Drying of the oily, in ether insoluble, residue affords 6.45 g of the title compound as a thick resin.

Workup

  1. customThe solvent is evaporated
  2. customthe residue is triturated with diethyl ether (2×15 ml)
  3. customto remove the excess of the phosphine
  4. dry with materialDrying of the oily, in ether insoluble

Sources & evidence

ORD record
ord-959ea3ef68d8401095e1b508b294dc7a
Source dataset
uspto-grants-2009_09
Patent number
US07595359B2

Reaction notes

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