Triphenylphosphine → HCID 10685511, compound

HRID 367095Notes

Reaction equation

HRID 367095 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]([N:39]1[CH2:42][CH2:41][C@H:40]1[CH2:43][OH:44])([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33].[Cl:45][C:46]1[C:51](O)=[CH:50][CH:49]=[CH:48][N:47]=1>C1COCC1>[Cl:45][C:46]1[C:51]([O:44][CH2:43][C@@H:40]2[CH2:41][CH2:42][N:39]2[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[CH:50][CH:49]=[CH:48][N:47]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 811362-Chloro-3-pyridinolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 10511797tert-butyl (2S)-2-(hydroxymethyl)azetidine-1-carboxylate

Product 1

HCID 10685511HCID 10685511, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of triphenylphosphine (1.73 g, 6.6 mmol) in THF (26 mL) was added diethyl azodicarboxylate (1.04 mL, 6.6 mmol) at 0° C., and the reaction mixture was stirred for 15 minutes. 1-BOC-2-(S)-azetidinemethanol (1.03 g, 5.5 mmol) and 2-chloro-3-pyridinol (785 mg, 6.0 mmol, Aldrich Chemical Co.) were then added. The reaction mixture was allowed to warm slowly to room temperature and stir overnight. Solvent was removed, and the residue was dissolved in ethyl acetate. The solution was washed with saturated aqueous K2CO3 and brine, dried over MgSO4 and concentrated. The residue was chromatographed on a silica gel column, eluting with ethyl acetate:hexane (1:4 to 1:1) to afford the title compound (611 mg). MS (DCI/NH3) m/z 299 (M+H)+.

Workup

  1. stirringstir overnight
  2. customSolvent was removed
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe solution was washed with saturated aqueous K2CO3 and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was chromatographed on a silica gel column
  8. washeluting with ethyl acetate:hexane (1:4 to 1:1)

Sources & evidence

ORD record
ord-eee07a24dfb041d4bd12688d0d85b886
Source dataset
uspto-grants-2000_10
Patent number
US06133253

Reaction notes

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