HCID 53847304, compound → HCID 22795184, compound
Reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]2[N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:6]=[CH:7][CH:8]=1>Br.O>[OH:2][C:3]1[CH:4]=[C:5]([C@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]2[N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:6]=[CH:7][CH:8]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
(1) The above oil (19g) was boiled in 47% hydrobromic acid (60 ml) for six hours. The cooled solution was diluted with water, washed with ether, basified and ether extracted. The dried extract was evaporated. The residue was triturated with petroleum ether (b.p. 40° to 60° C) and crystallised from petroleum ether (b.p. 60° to 80° C)/ ethyl acetate to give cis-2-(3-hydroxyphenyl)-1-pyrrolidinocyclohexane (12g), m.p. 124° to 126° C.