Ethyl (+/-)-10,11 dihydro-3-methoxy-5H-dibenzo[a,d]cycloheptene-10-acetate → Ethyl (+/-)-10,11-dihydro-7-fluoro-3-hydroxy-5H-dibenzo[a,d]cycloheptene-10-acetate

HRID 1369215Notes

Reaction equation

HRID 1369215 reaction equation
[F:1][C:2]1[CH:24]=[CH:23][C:5]2[CH:6]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:7][C:8]3[CH:14]=[CH:13][C:12]([O:15]C)=[CH:11][C:9]=3[CH2:10][C:4]=2[CH:3]=1.COC1C=CC2CC(CC(OCC)=O)C3C=CC=CC=3CC=2C=1>CO.C(Cl)Cl>[F:1][C:2]1[CH:24]=[CH:23][C:5]2[CH:6]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:7][C:8]3[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:9]=3[CH2:10][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 15462070Ethyl (+/-)-10,11 dihydro-3-methoxy-5H-dibenzo[a,d]cycloheptene-10-acetateHCID 54358299Ethyl (+/-)-10,11-dihydro-7-fluoro-3-methoxy-5H-dibenzo[a,d]cycloheptene-10-acetate

Product 1

HCID 53640576Ethyl (+/-)-10,11-dihydro-7-fluoro-3-hydroxy-5H-dibenzo[a,d]cycloheptene-10-acetate

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

According to the procedure of Preparation 10 (g), except substituting ethyl (±)-10,11-dihydro-7-fluoro3-methoxy-5H-dibenzo[a,d]cycloheptene-10-acetate for the ethyl (±)-10,11-dihydro-3-methoxy-5H-dibenzo[a,d]cycloheptene-10-acetate, the title compound was obtained as a white solid following silica gel chromatography (1% MeOH/CH2Cl2): MS (ES) m/e 315.0 (M+H)+, 332.0 (M+NH4)+.

Sources & evidence

ORD record
ord-97cc08c989434f95932444f1ad49e4a1
Source dataset
uspto-grants-2003_06
Patent number
US06576643B2

Reaction notes

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