2-Methyl-4-methoxyaniline → 1-tert-Butoxycarbonyl-4-[2-(4-methoxy-2-methyl-phenylsulfanyl)-5-fluoro-phenyl]-piperidine-4-ol

HRID 15233

Reaction equation

HRID 15233 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([OH:22])([C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=2[SH:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].I[C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:25]=1[CH3:32].COC1C=CC(N)=C(C)C=1>>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]([C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=2[S:21][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:25]=2[CH3:32])([OH:22])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 76102-Methyl-4-methoxyanilineHCID 131401601-Iodo-4-methoxy-2-methylbenzeneHCID 686821134-(5-Fluoro-2-mercapto-phenyl)-4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 686859691-tert-Butoxycarbonyl-4-[2-(4-methoxy-2-methyl-phenylsulfanyl)-5-fluoro-phenyl]-piperidine-4-ol

Procedure

Prepared from 4-hydroxy-4-(2-mercapto-5-fluoro-phenyl)-piperidine-1-carboxylic acid tert-butyl ester and 1-iodo-4-methoxy-2-methyl-benzene (prepared from 4-methoxy-2-methyl-phenylamine by diazotization according to the general procedure by Tunney and Stille J. Org. Chem. 1987, 52, 748-753).

Sources & evidence

ORD record
ord-0c2e9039a9924478966b3792f940004f
Source dataset
uspto-grants-2010_06
Patent number
US07732463B2

Linked notes

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