Methanesulfonyl chloride → HCID 86599987, compound

HRID 1455173Notes

Reaction equation

[CH3:1][S:2](Cl)(=[O:4])=[O:3].[F:6][C:7]([F:39])([F:38])[C:8]1[CH:9]=[C:10]([CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1)[CH2:11][N:12]([CH3:30])[C:13]([N:15]1[CH2:20][CH2:19][CH:18]([OH:21])[CH2:17][CH:16]1[C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=1[CH3:29])=[O:14]>C1COCC1>[CH3:1][S:2]([O:21][CH:18]1[CH2:19][CH2:20][N:15]([C:13](=[O:14])[N:12]([CH2:11][C:10]2[CH:9]=[C:8]([C:7]([F:6])([F:38])[F:39])[CH:33]=[C:32]([C:34]([F:35])([F:36])[F:37])[CH:31]=2)[CH3:30])[CH:16]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=2[CH3:29])[CH2:17]1)(=[O:4])=[O:3]

Participants

Conditions

Temperature: 0 °C

Procedure

Methanesulphonyl chloride (20 μL) was added to a solution of 2-(4-fluoro-2-methyl-phenyl)-4-hydroxy-piperidine-1-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methylamide (intermediate 11a and 11b—mixture of syn and anti diastereoisomers—85 mg) and TEA (50 μL) in dry THF (5 mL) previously cooled to 0° C. under a nitrogen atmosphere. After 1.5 hours, the solution was quenched with brine (4 mL) and extracted with AcOEt (3×5 mL). The organic layer was dried and concentrated in vacuo to a residue which was purified by flash chromatography (CH/AcOEt 7:3) to give methanesulfonic acid, 1-[(3,5-bis-trifluoromethyl-benzyl)-methyl-carbamoyl]-2-(4-fluoro-2-methyl-phenyl)-piperidin-4-yl ester in two fractions:

Workup

customthe solution was quenched with brine (4 mL)
extractionextracted with AcOEt (3×5 mL)
customThe organic layer was dried
concentrationconcentrated in vacuo to a residue which
customwas purified by flash chromatography (CH/AcOEt 7:3)

Sources & evidence

ORD record: ord-492640baa9ad44e698bdb45a3de695d2
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07482365B2

Reaction notes

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