1-(Triphenylphosphoranylidene)acetone → 1-(1-CBZ-2(S)-pyrrolidinyl)-1-buten-3-one

HRID 21762

Reaction equation

HRID 21762 reaction equation
[C:1]([N:11]1[CH2:17][CH2:16][CH2:15][C@H:12]1[CH:13]=O)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[CH:25][C:26](=[O:28])[CH3:27])C=CC=CC=1>C(Cl)Cl>[C:1]([N:11]1[CH2:17][CH2:16][CH2:15][C@H:12]1[CH:13]=[CH:25][C:26](=[O:28])[CH3:27])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

4

Reactant 2

HCID 150381-(Triphenylphosphoranylidene)acetoneHCID 11746545(S)-2-Formyl-pyrrolidine-1-carboxylic acid benzyl ester

Product 1

HCID 572125031-(1-CBZ-2(S)-pyrrolidinyl)-1-buten-3-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 350 mg (1.50 mmol) sample of CBZ-L-prolinal, from step 23b above, dissolved in 5 mL of methylene chloride was added 576 mg of 1-triphenylphosphoranylidene-2-propanone (Aldrich, 1.81 mmmol). The reaction was stirred at room temperature for 45 min, then heated at reflux for 1.3 hr. The solution was cooled, and a precipitate formed. The mixture was extracted with methylene chloride (3×10 mL). The combined organics were washed with brine and dried over MgSO4. The residue was chromatographed on silica gel, eluting with 25-35% ether in hexane. The title compound was isolated by removal of solvent (279 mg). Anal. Calcd for C16H19NO3: C, 70.31; H, 7.01; N, 5.12; Found: C, 70.20; H, 7.02; N, 5.10.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1.3 hr
  3. temperatureThe solution was cooled
  4. customa precipitate formed
  5. extractionThe mixture was extracted with methylene chloride (3×10 mL)
  6. washThe combined organics were washed with brine
  7. dry with materialdried over MgSO4
  8. customThe residue was chromatographed on silica gel
  9. washeluting with 25-35% ether in hexane

Sources & evidence

ORD record
ord-06a782866b2142bbab42b1fe509254c7
Source dataset
uspto-grants-1995_06
Patent number
US05424444

Linked notes

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