Butyl nitrite → 1-Azabicyclo[3.2.2]nonan-3,4-dione-3-oxime

A solution of 1-azabicyclo[3.2.2]nonan-4-one (1.39 g, 10 mmol) in anhydrous tetrahydrofuran (20 mL) under nitrogen was cooled (-65° C.), and treated with n-butyl nitrite (1.30 mL, 11 mmol). 1.0N Lithium bis(trimethylsilyl)amide/THF (16 mL, 16 mmol) was added dropwise so as to keep the pot temperature below -58° C. After the addition was complete the mixture was warmed to room temperature over one h, stirred for 30 min, cooled on an ice bath, and treated with saturated ammonium chloride (6 mL). The solution was concentrated in vacuo, diluted with toluene, and reconcentrated to remove most of the water. The residue was chromatographed on silica gel (eluted with 5% methanol/methylene chloride, then with 10% methanol/methylene chloride), then triturated from ether to afford 1-azabicyclo[3.2.2]nonan-3,4-dione-3-oxime (0.92 g, 55%) as a white solid.

1. customthe pot temperature below -58° C
2. additionAfter the addition
3. temperaturecooled on an ice bath
4. concentrationThe solution was concentrated in vacuo
5. additiondiluted with toluene
6. customto remove most of the water
7. customThe residue was chromatographed on silica gel (
8. washeluted with 5% methanol/methylene chloride
9. customwith 10% methanol/methylene chloride), then triturated from ether

ORD record

ord-d1fe09b7a2324d5995309b4656b03e15

Source dataset

uspto-grants-1996_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05583221