Triphenylphosphine → HCID 60029861, compound

HRID 496402Notes

Reaction equation

HRID 496402 reaction equation
[OH:1][C:2]1[C:3]([CH2:13][O:14][CH2:15][CH2:16][CH3:17])=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.[N:18]1([CH2:23][C@@H:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)O)[CH:22]=[CH:21][N:20]=[CH:19]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[N+](C(OCC)=O)(C(OCC)=O)=[N-]>O1CCCC1>[N:18]1([CH2:23][C@H:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[O:1][C:2]2[C:3]([CH2:13][O:14][CH2:15][CH2:16][CH3:17])=[C:4]3[C:9](=[CH:10][CH:11]=2)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]3)[CH:22]=[CH:21][N:20]=[CH:19]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 707108(R)-2-Imidazol-1-yl-1-phenyl-ethanolHCID 14357405DiethyldiazodicarboxylateHCID 223247446-Hydroxy-5-propoxymethyl-3,4-dihydro-2H-naphthalen-1-one

Product 1

HCID 60029861HCID 60029861, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

According to step 2 in the method of example 19a, 6-Hydroxy-5-propoxymethyl-3,4-dihydro-2H-naphthalen-1-one (0.123 g, 0.53 mmol), (R)-2-Imidazol-1-yl-1-phenyl-ethanol (0.131 g, 0.7 mmol), triphenylphosphine resin (0.620 g, loading 1.24 mmol/g, Argonaut Technologies), diethyl diazodicarboxylate (0.121 ml, 0.77 mmol, Aldrich Chemical) and freshly distilled tetrahydrofuran (5 ml, Aldrich Chemical) were combined in a 2 dram screw topped vial with a teflon lined cap. After mixing on an inverting mixer at 25° C. for 16 hrs., the resin was removed by gravity filtration and mixture concentrated in vacuo to a yellow-brown syrup. The residue was dissolved in methanol (5 ml) and macroporous polystyrene sulfonic acid resin (0.583 g, loading 1.5 mmol/g, Argonaut Technologies) added. After mixing for 2 hrs. at 25° C., the resin was collected by gravity filtration, washed with methanol (2×5 ml). Elution of product from the resin with 2.0 M ammonia in methanol (5 ml, Aldrich) and concentration in vacuo yielded 158 mg yellow glass compound. Low resolution mass spectroscopy m/z (APCI) 405 [M+H]+.

Workup

  1. customlined cap
  2. additionAfter mixing on an inverting mixer at 25° C. for 16 hrs
  3. custom, the resin was removed by gravity filtration and mixture
  4. concentrationconcentrated in vacuo to a yellow-brown syrup
  5. dissolutionThe residue was dissolved in methanol (5 ml)
  6. additionmacroporous polystyrene sulfonic acid resin (0.583 g, loading 1.5 mmol/g, Argonaut Technologies) added
  7. additionAfter mixing for 2 hrs
  8. filtrationat 25° C., the resin was collected by gravity filtration
  9. washwashed with methanol (2×5 ml)
  10. washElution of product from the resin
  11. concentrationwith 2.0 M ammonia in methanol (5 ml, Aldrich) and concentration in vacuo

Sources & evidence

ORD record
ord-a7055b73e54345bab9dd581f84ce3b25
Source dataset
uspto-grants-2005_09
Patent number
US06943183B2

Reaction notes

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