Hydrogen Sulfide → 3-Hydroxy-3-mercaptomethylquinuclidine

Reaction equation

CC1[S:13][CH2:12][C:4]2([CH:9]3[CH2:10][CH2:11][N:6]([CH2:7][CH2:8]3)[CH2:5]2)[O:3]1.C=C1C2CCN(CC2)C1.S>>[OH:3][C:4]1([CH2:12][SH:13])[CH:9]2[CH2:10][CH2:11][N:6]([CH2:7][CH2:8]2)[CH2:5]1

Participants

Reactant 3

HCID 402Hydrogen Sulfide

HCID 2684Evoxac

HCID 1408933-Methylenequinuclidine

Product 1

HCID 111267633-Hydroxy-3-mercaptomethylquinuclidine

Procedure

U.S. Pat. No. 4,855,290 describes a process for the preparation of 2-methylspiro(1,3-oxathiolane-5,3′-quinuclidine) (1), which comprises the preparation of the epoxide of 3-methylenequinuclidine, which is subsequently reacted with hydrogen sulfide to produce 3-hydroxy-3-mercaptomethylquinuclidine and is condensed with acetaldehyde in the presence of a Lewis acid (e.g. boron trifluoride etherate) to provide 2-methylspiro(1,3-oxathiolane-5,3′-quinuclidine).

Sources & evidence

ORD record: ord-883709d3ae574ada93593ff5ee04ea8b
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835638B2

Reaction notes

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