Perfluoro-1-butanesulfonyl fluoride → 4-[2-(Nonafluorobutane-1-sulfonyloxy)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 2244041Notes

Reaction equation

HRID 2244041 reaction equation
[F:1][C:2]([F:17])([C:13]([F:16])([F:15])[F:14])[C:3]([F:12])([F:11])[C:4]([F:10])([F:9])[S:5](F)(=[O:7])=[O:6].C(N(C(C)C)C(C)C)C.[C:27]([O:31][C:32]([N:34]1[CH2:39][CH2:38][CH:37]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=2[OH:46])[CH2:36][CH2:35]1)=[O:33])([CH3:30])([CH3:29])[CH3:28]>CN(C1C=CN=CC=1)C.ClCCCl>[C:27]([O:31][C:32]([N:34]1[CH2:35][CH2:36][CH:37]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=2[O:46][S:5]([C:4]([F:9])([F:10])[C:3]([F:11])([F:12])[C:2]([F:1])([F:17])[C:13]([F:16])([F:15])[F:14])(=[O:7])=[O:6])[CH2:38][CH2:39]1)=[O:33])([CH3:30])([CH3:28])[CH3:29]

Participants

6

Reactant 3

HCID 67814Perfluoro-1-butanesulfonyl fluorideHCID 81531DiisopropylethylamineHCID 17174861Tert-butyl 4-(2-hydroxyphenyl)piperidine-1-carboxylate

Product 1

HCID 866181014-[2-(Nonafluorobutane-1-sulfonyloxy)-phenyl]-piperidine-1-carboxylic acid tert-butyl esterYield 57%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolvent

Procedure

Nonafluoro-butane-1-sulfonyl fluoride (2.71 mL; 15.1 mmol) was added to a mixture of ethyl-diisopropyl-amine (2.87 mL; 16.5 mmol), 4-(N,N-dimethylamino)-pyridine (25 mg) and 4-(2-hydroxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (3.81 g; 13.7 mmol) in 50 ml 1,2-dichloro-ethane at 0° C. under argon. The reaction mixture was allowed to warm to room temperature and stirred 16 hours. The reaction mixture was extracted with water (100 mL) and brine (100 mL). The combined aqueous phases were extracted with ethyl acetate (100 mL). The combined organic phases were washed with brine (100 mL), dried with MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography (silica gel; ethyl acetate/heptane) to give 4.34 g 4-[2-(nonafluorobutane-1-sulfonyloxy)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester (7.76 mmol; 57%).

Workup

  1. extractionThe reaction mixture was extracted with water (100 mL) and brine (100 mL)
  2. extractionThe combined aqueous phases were extracted with ethyl acetate (100 mL)
  3. washThe combined organic phases were washed with brine (100 mL)
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (silica gel; ethyl acetate/heptane)

Sources & evidence

ORD record
ord-06a5508521b34088893b732620cb1898
Source dataset
uspto-grants-2010_03
Patent number
US07678800B2

Reaction notes

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