Toluene → [(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]sulfanylmethanethioic S-acid

HRID 222145Notes

Reaction equation

[CH3:1][N:2]1[CH:6]2[CH2:7][CH:8](OS(C)(=O)=O)[CH2:9][CH:3]1[CH2:4][CH2:5]2.C([O:17][C:18]([S-:20])=[S:19])C.[Na+].C1(C)C=CC=CC=1>O>[CH3:1][N:2]1[C@@H:3]2[CH2:9][CH:8]([S:19][C:18]([SH:20])=[O:17])[CH2:7][C@H:6]1[CH2:5][CH2:4]2

Participants

Conditions

Temperature: 30 °C

Procedure

Tropine-3-mesylate (25 g, 0.114 mol) and sodium ethylxanthate (19.7 g, 0.137 mol) were added to stirred toluene (0.075 L) under nitrogen. The stirred mixture was maintained at 30° C. for 6 h. Water (0.05 L) was added and after 15 min stirring the phases were separated. The toluene phase, containing the title compound, was used directly in the preparation of tropine-3-thiol as in Step 4b.

Workup

customwere separated
additionThe toluene phase, containing the title compound
customwas used directly in the preparation of tropine-3-thiol as in Step 4b

Sources & evidence

ORD record: ord-d178b9e2d1b04113869f3d398d99ef7a
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207191B2

Reaction notes

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