Triphenylphosphine → 5-(1-Ethyl-propoxymethyl)-6-((S)-2-imidazol-1-yl-1-phenyl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one

HRID 496404Notes

Reaction equation

HRID 496404 reaction equation
[CH2:1]([CH:3]([O:6][CH2:7][C:8]1[C:17]([OH:18])=[CH:16][CH:15]=[C:14]2[C:9]=1[CH2:10][CH2:11][CH2:12][C:13]2=[O:19])[CH2:4][CH3:5])[CH3:2].[N:20]1([CH2:25][C@@H:26]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)O)[CH:24]=[CH:23][N:22]=[CH:21]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[N+](C(OCC)=O)(C(OCC)=O)=[N-]>O1CCCC1>[CH2:1]([CH:3]([O:6][CH2:7][C:8]1[C:17]([O:18][C@@H:26]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:25][N:20]2[CH:24]=[CH:23][N:22]=[CH:21]2)=[CH:16][CH:15]=[C:14]2[C:9]=1[CH2:10][CH2:11][CH2:12][C:13]2=[O:19])[CH2:4][CH3:5])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 707108(R)-2-Imidazol-1-yl-1-phenyl-ethanolHCID 14357405DiethyldiazodicarboxylateHCID 697370915-(1-Ethyl-propoxymethyl)-6-hydroxy-3,4-dihydro-2H-naphthalen-1-one

Product 1

HCID 600299405-(1-Ethyl-propoxymethyl)-6-((S)-2-imidazol-1-yl-1-phenyl-ethoxy)-3,4-dihydro-2H-naphthalen-1-oneYield 60.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

According to step 2 in the method of example 19, 5-(1-Ethyl-propoxymethyl)-6-hydroxy-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 139 mg brown glass compound. Low resolution mass spectroscopy m/z (APCI) 433 [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-ebf34bfb04cf4312801c1c70bd283211
Source dataset
uspto-grants-2005_09
Patent number
US06943183B2

Reaction notes

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