Tetrahydrofuran → Benzyl 4-{3,3,3-trifluoro-2-[(methylsulfonyl)oxy]propoxy}piperidine-1-carboxylate

HRID 2368103Notes

Reaction equation

[F:1][C:2]([F:24])([F:23])[CH:3]([OH:22])[CH2:4][O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH2:8][CH2:7]1.[S:25](Cl)([CH3:28])(=[O:27])=[O:26].C(N(CC)CC)C.C1COCC1>O>[F:24][C:2]([F:1])([F:23])[CH:3]([O:22][S:25]([CH3:28])(=[O:27])=[O:26])[CH2:4][O:5][CH:6]1[CH2:7][CH2:8][N:9]([C:12]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:13])[CH2:10][CH2:11]1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of benzyl 4-(3,3,3-trifluoro-2-hydroxypropoxy)piperidine-1-carboxylate (983 mg), mesyl chloride (0.438 mL), triethylamine (0.789 mL) and THF (10 mL) was stirred at 0° C. for 1 hr, and then at room temperature overnight. Water was added thereto, and the obtained mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.12 g).

Workup

customat room temperature
customovernight
extractionthe obtained mixture was extracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-645bdbfeb14843f8810bf00ef15d3efb
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703758B2

Reaction notes

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