反应详情

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]+.

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