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Phenylboronic acid pinacol ester → 1-[(4-Methylphenyl)sulfonyl]-4-phenylpiperidine

HRID 2027433
Notes
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Reaction equation

HRID 2027433 reaction equation
[CH3:1][c:2]1[cH:7][cH:6][c:5]([S:8]([N:11]2[CH2:16][CH2:15][CH:14]([C:17](ON3C(=O)c(c4C3=O)c(Cl)c(Cl)c(Cl)c4Cl)=O)[CH2:13][CH2:12]2)(=[O:10])=[O:9])[cH:4][cH:3]1.CC1(C(C)(C)OB(c2[cH:22][cH:21][cH:20][cH:19][cH:18]2)O1)C>>[CH3:1][c:2]1[cH:7][cH:6][c:5]([S:8]([N:11]2[CH2:16][CH2:15][CH:14]([c:17]3[cH:22][cH:21][cH:20][cH:19][cH:18]3)[CH2:13][CH2:12]2)(=[O:10])=[O:9])[cH:4][cH:3]1
ParticipantsConditionsSources & evidenceReaction notes

Participants

8

Reactant 2

HCID 570673Phenylboronic acid pinacol esterHCID 1682674794,5,6,7-Tetrachloro-1,3-dioxoisoindolin-2-yl 1-tosylpiperidine-4-carboxylate

Product 1

HCID 41684661-[(4-Methylphenyl)sulfonyl]-4-phenylpiperidine

Reagents, catalysts & solvents 5

HCID 23683543Potassium t-amylateReagentHCID 5483663Ferric acetylacetonateCatalyst

Conditions

Temperature
60 °C

Sources & evidence

ORD record
ord-c789fbb03be845da9e61102955cefa26
Source dataset
39k HTE dataset from Pfizer
DOI
10.1038/s41557
Original link
View source

Reaction notes

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On this pageParticipantsConditionsSources & evidenceReaction notes
HCID 24884872
[(1R,2R)-2-[bis(3,5-dimethylphenyl)phosphanylmethyl]cyclobutyl]methyl-bis(3,5-dimethylphenyl)phosphane
Catalyst
HCID 8028TetrahydrofuranSolvent
HCID 117669-PhenylanthraceneInternal standard