Trifluoroacetic acid → 2-(4-((1,4-Diazepan-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol

HRID 1807748Notes

Reaction equation

HRID 1807748 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]([C:9]1[CH:29]=[CH:28][C:12]([CH2:13][N:14]2[CH2:20][CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]2)=[CH:11][CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].FC(F)(F)C(O)=O>ClCCl>[N:14]1([CH2:13][C:12]2[CH:28]=[CH:29][C:9]([C:3]([OH:8])([C:2]([F:1])([F:30])[F:31])[C:4]([F:6])([F:7])[F:5])=[CH:10][CH:11]=2)[CH2:20][CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86638560tert-Butyl 4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)-1,4-diazepane-1-carboxylate

Product 1

HCID 866385612-(4-((1,4-Diazepan-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-olYield 76.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl 4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)-1,4-diazepane-1-carboxylate (15.34 mmol, 7 g), dichloromethane (15 mL) and trifluoroacetic acid (15.00 mL) was stirred for 24 hours. The reaction was purified by SCX chromatography to give the title compound (4.2 g). MS (ESI) m/z 357.1 [M+H]+

Workup

  1. customThe reaction was purified by SCX chromatography

Sources & evidence

ORD record
ord-f78b2ed5301843eab0d7c8d00fd8568b
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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