反应详情

1,2,3,4-Tetrahydro-1,4-methano-naphthalene-2,3-diol (40 g, 227.3 mmol) was stirred in H2O (1050 mL) and 1,2-dichloroethane (DCE) (420 mL) in a 2 L round bottom flask under nitrogen with cool water bath (˜10° C.). To this sodium periodate (NalO4) (51 g. 239 mmol) and triethylbenzyl ammonium chloride (Et3BnNCl) (50 mg) were added. The resulting mixture was stirred for 1 hour (slight initial exotherm), then the layers were separated and the aqueous layer was extracted with DCE (200 mL). The organic layer was washed with H2O (4×200 mL, or until no reaction to starch iodide is observed in the aqueous wash) then dried through a cotton plug. To this was added benzyl amine (25.5 g, 238.6 mmol) and the mixture was stirred for 2 minutes then immediately transferred into the sodium triacetoxyborohydride NaHB(OAc)3/DCE (see below) over 10 minutes.

1. custom(˜10° C.)
2. customwere separated
3. extractionthe aqueous layer was extracted with DCE (200 mL)
4. washThe organic layer was washed with H2O (4×200 mL
5. customuntil no reaction to starch iodide
6. washaqueous wash)
7. customthen dried through a cotton plug
8. stirringthe mixture was stirred for 2 minutes