Phenylhydrazine → cis-1,2,2a,3,4,9-hexahydro-9bH-cyclobuta[a]carbazole-9b-acetic acid ethyl ester

HRID 2351371Notes

Reaction equation

HRID 2351371 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C@@:6]12[CH2:13][CH2:12][C@@H:11]1[CH2:10][CH2:9][CH2:8][C:7]2=O)[CH3:2].[C:16]1([NH:22]N)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C@:6]12[CH2:13][CH2:12][C@H:11]1[CH2:10][CH2:9][C:8]1[C:17]3[C:16]([NH:22][C:7]=12)=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH3:2]

Participants

3

Reactant 2

HCID 7516PhenylhydrazineHCID 53960823cis-2-Oxobicyclo[4.2.0]octane-1-acetic acid ethyl ester

Product 1

HCID 86742523cis-1,2,2a,3,4,9-hexahydro-9bH-cyclobuta[a]carbazole-9b-acetic acid ethyl esterYield 16.6%

Procedure

cis-2-Oxobicyclo[4.2.0]octane-1-acetic acid ethyl ester (3.5 g, 17.01 mmol) and phenylhydrazine (1.9 mL, 18.8 mmol) were allowed to react according to the procedure of Example 2. Flash chromatography (SiO2, 10% EtOAC/petroleum ether) afforded 0.798 g (16%) of cis-1,2,2a,3,4,9-hexahydro-9bH-cyclobuta[a]carbazole-9b-acetic acid ethyl ester.

Workup

  1. customto react

Sources & evidence

ORD record
ord-e2586ed479414338aadbc6a4cf773840
Source dataset
uspto-grants-1989_10
Patent number
US04873257

Reaction notes

Loading…