Triphenylphosphine → HCID 62349642, compound

HRID 1393050Notes

Reaction equation

HRID 1393050 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:8])=[N:6][CH:7]=1.O[CH:10]1[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH:10]2[CH2:14][CH2:13][NH:12][CH2:11]2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 44169391-Boc-3-pyrrolidinolHCID 1785160645-chloropyridin-2-ol

Product 1

HCID 62349642HCID 62349642, compound

Reagents, catalysts & solvents 1

HCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

To a stirred solution of 5-chloro-2-pyridinol (323.9 mg; 2.5 mmol), tert-butyl 3-hydroxy-1-pyrrolidinecarboxylate (468.0 mg, 2.5 mmol) and triphenylphosphine polymer bound (1 g, 3 mmol) in THF/CH2Cl2 (1:1, 5 ml) slowly was added diethyl azodicarboxylate (435.5 mg 2.5 mmol). The solution was slowly stirred overnight Resin was then removed by filtration and washed with THF. The combined filtrates were evaporated to dryness. The resulting residue was purified by RP-HPLC (10-40% CH3CN). The pure material was treated with 95% TFA/5% H2O, 30 min. The TFA phase was then evaporated to give the desired product as a solid.

Workup

  1. customResin was then removed by filtration
  2. washwashed with THF
  3. customThe combined filtrates were evaporated to dryness
  4. customThe resulting residue was purified by RP-HPLC (10-40% CH3CN)
  5. additionThe pure material was treated with 95% TFA/5% H2O, 30 min
  6. customThe TFA phase was then evaporated

Sources & evidence

ORD record
ord-0c8ba81873fc4d31b36ed3f90027ad3a
Source dataset
uspto-grants-2008_03
Patent number
US07345063B2

Reaction notes

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