psi-Pelletierine → 9-Methyl-9-aza-bicyclo[3.3.1]nonan-3-one oxime hydrochloride

HRID 969808

Reaction equation

HRID 969808 reaction equation
[CH3:1][N:2]1[CH:7]2[CH2:8][CH2:9][CH2:10][CH:3]1[CH2:4][C:5](=O)[CH2:6]2.[ClH:12].[NH2:13][OH:14]>CO>[ClH:12].[CH3:1][N:2]1[CH:7]2[CH2:8][CH2:9][CH2:10][CH:3]1[CH2:4][C:5](=[N:13][OH:14])[CH2:6]2

Participants

4

Reactant 2

HCID 11096psi-PelletierineHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 866072389-Methyl-9-aza-bicyclo[3.3.1]nonan-3-one oxime hydrochlorideYield 76.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 9-methyl-9-aza-bicyclo[3.3.1]nonan-3-one (0.658 g, 4.29 mmol) and hydroxylamine hydrochloride (0.312 g, 4.49 mmol) in methanol (6 mL) was stirred for 20 h at room temperature, during which time a white precipitate formed. This solid was collected by filtration, rinsed with additional methanol (2×10 mL), and dried under vacuum for 1 h to afford 0.672 g (76% yield) of 9-methyl-9-aza-bicyclo[3.3.1]nonan-3-one oxime hydrochloride as a white solid: 1H NMR (300 MHz, DMSO-d6) d 10.82 (s, 1H), 3.71-3.52 (m, 2H), 3.34-3.23 (m, 1H), 3.12 (d, J=17.5 Hz, 1H), 2.90-2.79 (m, 3H), 2.73-2.55 (m, 1H), 2.42 (d, J=16.8 Hz, 1H), 2.27-2.05 (m, 2H), 1.87-1.42 (m, 4H); MS (ESI) m/z 169 [M+H]+

Workup

  1. customformed
  2. filtrationThis solid was collected by filtration
  3. washrinsed with additional methanol (2×10 mL)
  4. customdried under vacuum for 1 h

Sources & evidence

ORD record
ord-a943870aa6d74f23b1f5c3c1f3846ca9
Source dataset
uspto-grants-2007_12
Patent number
US07307094B2

Linked notes

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