1-Azatricyclo(3.3.1.1,3,7)decan-4-one → HCID 87333855, compound

HRID 1697440Notes

Reaction equation

HRID 1697440 reaction equation
Cl.F[C:3](F)([O:15][NH2:16])[C:4]1[C:9]([F:10])=[C:8]([F:11])[C:7]([F:12])=[C:6]([F:13])[C:5]=1[F:14].[N:18]12[CH2:27][CH:22]3[CH2:23][CH:24]([CH2:26][CH:20]([C:21]3=O)[CH2:19]1)[CH2:25]2>C(O)C>[F:10][C:9]1[C:4]([CH2:3][O:15][N:16]=[C:21]2[CH:22]3[CH2:27][N:18]4[CH2:25][CH:24]([CH2:26][CH:20]2[CH2:19]4)[CH2:23]3)=[C:5]([F:14])[C:6]([F:13])=[C:7]([F:12])[C:8]=1[F:11]

Participants

4

Reactant 2

HCID 1426421-Azatricyclo(3.3.1.1,3,7)decan-4-oneHCID 86623776HCID 86623776, compound

Product 1

HCID 87333855HCID 87333855, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Solid O-(perfluorobenzyl)hydroxylamine HCl (167 mg, 0.669 mmol, Aldrich Chemical Co.) was added to a warm solution of 1-azatricyclo[3.3.1.13,7]decan-4-one (102 mg, 0.675 mmol) (prepared as reported in: Becker, D. P. and Flynn, D. L. Synthesis 1992, 1080-1082) in ethanol (1 mL). The mixture was swirled with warming to dissolve all solids. The nearly colorless solution was allowed to cool to room temperature overnight. The solvent was removed under vacuum, and the residue was crystallized from 10% ethanol in ethyl acetate (3 mL) to provide the title compound as hydrochloride salt. 1H NMR (300 MHz, CD3OD) δ 1.87-2.06 (m, 2 H), 2.22 (q, J=3 Hz, 1 H), 2.24-2.37 (m, 2 H), 2.83 (s, 1H), 3.30, (m, 1H), 3.43-3.57 (m, 2 H), 3.64 (s, 2 H), 3.66-3.78 (m, 2 H), 5.15-5.24 ppm (m, 2 H); MS (DCI/NH3) m/z 347 (M+H)+; Anal. C16H15N2OF5—HCl requires C, 50.21; H, 4.21; N, 7.32. Found C, 50.20; H, 3.99; N, 7.22.

Workup

  1. temperaturewith warming
  2. dissolutionto dissolve all solids
  3. customThe solvent was removed under vacuum
  4. customthe residue was crystallized from 10% ethanol in ethyl acetate (3 mL)

Sources & evidence

ORD record
ord-ebd0e033bb824d7aa4a5b1643039efff
Source dataset
uspto-grants-2012_04
Patent number
US08163915B2

Reaction notes

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