Triphenylphosphine → HCID 54565828, compound

HRID 1416596Notes

Reaction equation

HRID 1416596 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[C:32]([O:36][C:37]([N:39]1[CH2:43][CH2:42][CH2:41][C@H:40]1[CH2:44][OH:45])=[O:38])([CH3:35])([CH3:34])[CH3:33].[CH3:46][C:47]1[N:52]=[CH:51][C:50](O)=[CH:49][CH:48]=1>C1COCC1>[CH3:46][C:47]1[N:52]=[CH:51][C:50]([O:45][CH2:44][C@@H:40]2[CH2:41][CH2:42][CH2:43][N:39]2[C:37]([O:36][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:38])=[CH:49][CH:48]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 142752-Methyl-5-hydroxypyridineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 643448(S)-(-)-N-Boc-prolinol

Product 1

HCID 54565828HCID 54565828, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of triphenylphosphine (3.83 g, 14.60 mmol) in 40 mL of anhydrous THF at 0° C. was added diethyl azodicarboxylate (2.3 mL, 14.60 mmol) dropwise. The mixture was stirred at 0° C. for 30 minutes, then brought to room temperature. (S)-1-t-Butoxycarbonyl-2-pyrrolidinemethanol (1.96 g, 9.75 mmol, Aldrich Chemical Co.) and 6-methyl-3-pyridinol (Aldrich Chemical Co.,1.60 g, 14.60 mmol) were added to the reaction vessel, and the mixture was stirred for 16 hours. Solvent was removed in vacuo, and the residue was diluted with hexane and sonicated for 30 minutes. The resulting precipitate was filtered and washed with hexane. The hexane was removed in vacuo. The residue was purified by silica gel flash chromatography using a gradient from 100% hexane to a 1:1 solution of ethyl acetate/hexane (100% Hex, 10%EtOAc/Hex, 20%EtOAc/Hex, 1:1 EtOAc/Hex) to give 1.61 g (57%) of the title compound as a pale yellow oil. TLC Rf=0.42 (1:1 EtOAc/Hex). MS (DCI/NH3) m/e: 293 (M+H)+.

Workup

  1. custombrought to room temperature
  2. stirringthe mixture was stirred for 16 hours
  3. customSolvent was removed in vacuo
  4. additionthe residue was diluted with hexane
  5. customsonicated for 30 minutes
  6. filtrationThe resulting precipitate was filtered
  7. washwashed with hexane
  8. customThe hexane was removed in vacuo
  9. customThe residue was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-5deba47e48574699aac2a63145c99054
Source dataset
uspto-grants-1999_06
Patent number
US05914328

Reaction notes

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