9-Methyl-3-thia-9-azabicyclo[3.3.1]nonan-7-one → 9-Methyl-3-thia-9-aza-bicyclo[3.3.1]nonan-7-one oxime

HRID 1928809Notes

Reaction equation

[CH3:1][N:2]1[CH:7]2[CH2:8][C:9](=O)[CH2:10][CH:3]1[CH2:4][S:5][CH2:6]2.Cl.[NH2:13][OH:14]>C(O)C>[CH3:1][N:2]1[CH:7]2[CH2:8][C:9](=[N:13][OH:14])[CH2:10][CH:3]1[CH2:4][S:5][CH2:6]2

Participants

Conditions

Temperature: 23 °C

Procedure

A mixture of 9-Methyl-3-thia-9-aza-bicyclo[3.3.1]nonan-7-one (CAS no: 99709-31-6) (3.0 g, 17.5 mmol) in ethanol (100 mL) and hydroxylamine hydrochloride (1.58 g, 22.8 mmol) was refluxed for 16 h. Cooled to 23° C., the precipitate was filtered off, washed with ethanol and diethyl ether and dried in vacuum to give a light brown solid (2.5 g), which was partitioned between dichloromethane and sodium carbonate solution, the organic layers dried over Na2SO4, filtered and the solvents evaporated to give the title compound as a white solid. (1.3 g, 40%); MS: m/e=187.1 (M+H+).

Workup

filtrationthe precipitate was filtered off
washwashed with ethanol and diethyl ether
customdried in vacuum

Sources & evidence

ORD record: ord-0445bd3e9d78474d8dfe0e014f1ed446
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183380B2

Reaction notes

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