Triethylborane → (S)-tert-Butyl 2-(3-(perfluorophenoxysulfonyl)propyl)pyrrolidine-1-carboxylate

HRID 1643453Notes

Reaction equation

HRID 1643453 reaction equation
[PH2](O)=O.C(N1CCCCC1)C.[CH2:12]=[CH:13][S:14]([O:17][C:18]1[C:23]([F:24])=[C:22]([F:25])[C:21]([F:26])=[C:20]([F:27])[C:19]=1[F:28])(=[O:16])=[O:15].I[CH2:30][C@@H:31]1[CH2:35][CH2:34][CH2:33][N:32]1[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37].C(B(CC)CC)C>C(Cl)Cl>[F:24][C:23]1[C:22]([F:25])=[C:21]([F:26])[C:20]([F:27])=[C:19]([F:28])[C:18]=1[O:17][S:14]([CH2:13][CH2:12][CH2:30][C@@H:31]1[CH2:35][CH2:34][CH2:33][N:32]1[C:36]([O:38][C:39]([CH3:40])([CH3:42])[CH3:41])=[O:37])(=[O:16])=[O:15]

Participants

6

Reactant 4

HCID 7357Triethylborane2×HCID 2763990Pentafluorophenyl vinylsulfonateHCID 11312942(S)-2-Iodomethyl-pyrrolidine-1-carboxylic acid tert-butyl esterHCID 178462538HCID 178462538, compound

Product 1

HCID 59367744(S)-tert-Butyl 2-(3-(perfluorophenoxysulfonyl)propyl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Ethylpiperidine hypophosphite (30 g, 168 mmol) were weighed into the reaction flask under an inert gas, and methylene chloride (100 ml) was added. The solution was cooled with ice-water and 2,3,4,5,6-pentafluorophenyl 1-ethylenesulfonate (5.06 g, 18.5 mmol) [Org. Lett.; 2002; 4(15); 2549-2551] and (S)-tert-butyl 2-(iodomethyl)pyrrolidine-1-carboxylate (5.22 g, 16.8 mmol) was added at 10° C. Triethylborane solution (1.6 ml, 1 mol/l) was added and compressed air was then passed through the mixture for 5 sec. After stirring for min the addition of triethylborane solution-compressed air was repeated with the same amount. The cooling bath was removed, the mixture was stirred for 10 min and the reaction mixture was then washed with water (20 ml) and saturated sodium chloride solution (20 ml), dried over sodium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (silica gel) with hexane/diethyl ether (2:1). Yield: 2.81 g (36%)

Workup

  1. additionwas added
  2. additionwas added at 10° C
  3. customThe cooling bath was removed
  4. stirringthe mixture was stirred for 10 min
  5. washthe reaction mixture was then washed with water (20 ml) and saturated sodium chloride solution (20 ml)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by column chromatography (silica gel) with hexane/diethyl ether (2:1)

Sources & evidence

ORD record
ord-cc80e06a145948fcb30a60cc2204b22e
Source dataset
uspto-grants-2012_02
Patent number
US08119805B2

Reaction notes

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