Reacción #2269956

Ecuación de reacción

benzyl amine

1,2,3,4-Tetrahydro-1,4-methano-naphthalene-2,3-diol

1,2-dichloroethane

sodium periodate

→

10-Benzyl-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-triene

Disolventes

H2O

Condiciones de reacción

Tratamiento posterior

1. 1
   Otro(˜10° C.)
2. 2
   Otrowere separated
3. 3
   Extracciónthe aqueous layer was extracted with DCE (200 mL)
4. 4
   LavadoThe organic layer was washed with H2O (4×200 mL
5. 5
   Otrountil no reaction to starch iodide
6. 6
   Lavadoaqueous wash)
7. 7
   Otrothen dried through a cotton plug
8. 8
   workup.STIRRINGthe mixture was stirred for 2 minutes

Procedimiento

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 (NaIO4) (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.

Fuente