Ammonia → HCID 21882838, compound

Participants

Reaction Steps

To methanol (1 litre) saturated with ammonia cooled to 0° C. were added ammonium hydroxide (60.4 ml), ammonium chloride (30 g), sodium cyanide (3 g) and 2-benzyloxy-5,6,7,8,9,10-hexahydro-6,9-methanobenzo[α][8]annulen-11-one (9.5 g). The reaction was stirred vigorously for 1 hr to ensure complete dissolution and left standing at 3° C. for 18 hrs. The precipitate was filtered, washed with ice-chilled water, ice-chilled methanol and dried in vacuo at 50° C. to give the title compound (8.4 g, 81%) as a white solid (360 MHz δd6-DMSO) 1.17 (2H, m), 1.84 (2H, m), 2.38 (2H, m), 2.78 (2H, m), 3.40 (2H, m), 5.03 (2H, s), 6.73 (2H, m), 6.98 (1H, d, J=8.2), 7.37 (5H, m). Step 3: [6S/R,9R/S,11R/S] 2′,3′,4′,5,5′,6,7,8,9,10-decahydro-2-benzyloxy-spiro [6,9-methanobenzocyclooctene-11,3′-[1,2,5]thiadiazole]1′,1′-dioxide.

Provenance & Evidence