Water → HCID 69057681, compound

HRID 1727177Notes

Reaction equation

S(O[CH:7]1[CH2:13][CH:12]2[N:14]([CH3:15])[CH:9]([CH2:10][CH2:11]2)[CH2:8]1)(OC)(=O)=O.[H-].[Na+].[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([SH:26])=[CH:22][CH:21]=1.O>O1CCCC1>[CH3:15][N:14]1[CH:9]2[CH2:10][CH2:11][CH:12]1[CH2:13][CH:7]([S:26][C:23]1[CH:24]=[CH:25][C:20]([O:19][CH3:18])=[CH:21][CH:22]=1)[CH2:8]2

Participants

Conditions

Temperature: 30 °C

Procedure

To a solution of methyl 8-methyl-8-azabicyclo[3.2.1]oct-3-yl sulfate (Preparation 13, 35 g, 0.16 mol) in tetrahydrofuran (300 ml) was added with cooling to 0° C. sodium hydride (60% dispersion in oil, 7 g, 0.17 mol). After complete addition, 4-methoxybenzene thiol (23.8 g, 0.16 mol) was added in tetrahydrofuran (300 ml). The reaction mixture was heated under reflux for 2 h and then cooled to 30° C. and water (250 ml) was added. The tetrahydrofuran was removed in vacuo, dichloromethane was added and the layers separated. The organic layer washed with water, sodium hydroxide (1 M solution), water, and saturated brine before drying (Na2SO4). The organic extracts were concentrated in vacuo to give the title compound (43.7 g, 100%).

Workup

temperatureThe reaction mixture was heated
temperatureunder reflux for 2 h
customThe tetrahydrofuran was removed in vacuo, dichloromethane
additionwas added
customthe layers separated
washThe organic layer washed with water, sodium hydroxide (1 M solution), water, and saturated brine
dry with materialbefore drying (Na2SO4)
concentrationThe organic extracts were concentrated in vacuo

Sources & evidence

ORD record: ord-21bef720a1cb43b3bd2ba80aa95c1958
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07494992B2

Reaction notes

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