Azepan-4-ol → Methyl 4-bromo-3-(4-hydroxyazepan-1-yl)sulfonyl-benzoate

HRID 1754300Notes

Reaction equation

[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[S:12](Cl)(=[O:14])=[O:13].[NH:16]1[CH2:22][CH2:21][CH2:20][CH:19]([OH:23])[CH2:18][CH2:17]1>C(Cl)Cl>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[S:12]([N:16]1[CH2:22][CH2:21][CH2:20][CH:19]([OH:23])[CH2:18][CH2:17]1)(=[O:14])=[O:13]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of methyl 4-bromo-3-chlorosulfonyl-benzoate (7.22 g, 23.03 mmol, 1.00 Eq) in DCM (100 mL) was added azepan-4-ol (2.65 g, 23.03 mmol, 1.00 Eq) and TEA (2.33 g, 23.03 mmol, 1.00 Eq). The resulting mixture was stirred at 25° C. until the starting material was consumed. The solvent was removed and the residue was purified by silica gel chromatography (PE:EA=1:1) to give desired compound methyl 4-bromo-3-(4-hydroxyazepan-1-yl)sulfonyl-benzoate (7.00 g, 17.85 mmol, 77.49% yield). LCMS: 393/395 [M+1].

Workup

customwas consumed
customThe solvent was removed
customthe residue was purified by silica gel chromatography (PE:EA=1:1)

Sources & evidence

ORD record: ord-131c3ad461b842a69d21fcb47ddda90b
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09169212B2

Reaction notes

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