Triphenylphosphine → HCID 66861063, compound

HRID 255154Notes

Reaction equation

HRID 255154 reaction equation
O[C@:2]1([C:12]([OH:14])=[O:13])[CH2:6][CH2:5][C:4]([CH2:8][OH:9])([CH3:7])[C:3]1([CH3:11])[CH3:10].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[CH3:7][C:4]12[C:3]([CH3:11])([CH3:10])[C@@:2]([C:12]([OH:14])=[O:13])([CH2:6][CH2:5]1)[O:9][CH2:8]2

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 66858910HCID 66858910, compound

Product 1

HCID 66861063HCID 66861063, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 222A (125 mg) and triphenylphosphine (366 mg) in tetrahydrofuran (10 mL) at 0° C. was added dropwise diisopropylazodicarboxylate (0.27 mL). The reaction mixture was allowed to warm to room temperature and stirred overnight. The mixture was partitioned between 1 N aqueous NaOH (10 mL) and ether (20 mL) and the layers separated. The aqueous phase was extracted twice with ether to remove non-polar organic extracts, then acidified with 1 N aqueous HCl and extracted with ether (3×). The organic extracts were dried (MgSO4), filtered and solvent evaporated to afford the title compound. 1H NMR (CDCl3, 300 MHz) δ ppm 0.93 (s, 3H), 0.95 (s, 3H), 1.04 (s, 3H), 1.5-1.6 (m, 1H), 1.73-1.85 (m 1H), 1.88-1.97 (m, 1H), 2.24-2.35 (m, 1H), 3.60 (d, 1H), 3.76 (dd, 1H).

Workup

  1. customThe mixture was partitioned between 1 N aqueous NaOH (10 mL) and ether (20 mL)
  2. customthe layers separated
  3. extractionThe aqueous phase was extracted twice with ether
  4. customto remove non-polar organic extracts
  5. extractionextracted with ether (3×)
  6. dry with materialThe organic extracts were dried (MgSO4)
  7. filtrationfiltered
  8. customsolvent evaporated

Sources & evidence

ORD record
ord-a5fb5c3cc7cf4d64ad4d21d86b8e6e50
Source dataset
uspto-grants-2011_01
Patent number
US07875639B2

Reaction notes

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