1,2-Dichloroethane → 3-Benzyl-2,3,4,5-tetrahydro-1H-1,5-methano-3-benzazepine

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Reaction Steps

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.

Provenance & Evidence