Triphenylphosphine → HCID 15341166, compound

HRID 442765Notes

Reaction equation

HRID 442765 reaction equation
O[C:2]1[CH:3]=[C:4]([C@@H:10]([C:18]2[CH:19]=[C:20]([CH:22]=[CH:23][CH:24]=2)N)[CH2:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH2:44]1[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[CH2:46][CH:45]1[OH:53].CCOC(/[N:59]=N/C(OCC)=O)=O>C1COCC1.C(OCC)(=O)C>[CH2:44]1[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[CH2:46][CH:45]1[O:53][C:2]1[CH:3]=[C:4]([C@@H:10]([C:18]2[CH:19]=[CH:20][C:22]([NH2:59])=[CH:23][CH:24]=2)[CH2:11][C:12]2[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

7

Reactant 4

HCID 11776Triphenylphosphine2×HCID 779362-Indanol2×HCID 5462977Diethyl azodicarboxylate2×HCID 21309138HCID 21309138, compound

Product 1

HCID 15341166HCID 15341166, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of Intermediate 1 (1.0 g, 3.1 mmol) in THF (25 ml) at RT was added PPh3 (820 mg, 1 eq), 2-indanol (419 mg, 1 eq) and the solution stirred for 10 min prior to the addition of DEAD (492 μl, 1 eq). The reaction mixture was stirred at this temperature for 65 h before the further addition of 2-indanol (419 mg), PPh3 (820 mg) and DEAD (492 μl ). The mixture was stirred for an additional 1.5 h then quenched by the addition of water (10 ml). The mixture was diluted with ethyl acetate (100 ml), washed with water (4×50 ml), brine (50 ml), dried (MgSO4), filtered and concentrated in vacuo to give a brown foam. The crude product was redissolved in ethyl acetate (50 ml) and extracted into hydrochloric acid (2×50 ml, 10% aq). The aqueous extract was basified (NaOH to pH>10) then extracted with ethyl acetate (2×100 ml). The extract was washed with water (2×50 ml), brine (50 ml), dried (MgSO4), filtered and concentrated in vacuo to give a white foam. This was subjected to column chromatography (SiO2 ; ethylacetate) to afford the title compound (856 mg, 63%) as a white foam. δH (CDCl3) 3.05-3.35 (6H, m), 3.77 (3H, s), 4.06 (1H, t, J 8.0 Hz), 5.08 (1H, m), 6.52 (2H, d, J 7.8 Hz), 6.63 (1H, d, J 7.6 Hz), 6.70 (1H, s), 6.76 (2H, s), 6.95 (2H, d, J 6.0 Hz), 7.07 (1H, t, J 7.7 Hz), 7.18 (4H, m), and 8.41 (2H, d, J 5.9 Hz). m/z (ESI) 437 (MH+, 100%), 459 (MNa+, 2).

Workup

  1. stirringThe mixture was stirred for an additional 1.5 h
  2. customthen quenched by the addition of water (10 ml)
  3. additionThe mixture was diluted with ethyl acetate (100 ml)
  4. washwashed with water (4×50 ml), brine (50 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a brown foam
  9. extractionextracted into hydrochloric acid (2×50 ml, 10% aq)
  10. extractionThe aqueous extract
  11. extractionthen extracted with ethyl acetate (2×100 ml)
  12. washThe extract was washed with water (2×50 ml), brine (50 ml)
  13. dry with materialdried (MgSO4)
  14. filtrationfiltered
  15. concentrationconcentrated in vacuo
  16. customto give a white foam

Sources & evidence

ORD record
ord-b518db9355944381817c262b9b7d6af4
Source dataset
uspto-grants-1999_04
Patent number
US05891896

Reaction notes

Loading…