1,8-Diazabicyclo(5.4.0)undec-7-ene → tert-Butyl 3-(2-(4-(2-(pyrrolidin-1-yl)ethyl)piperidin-1-ylsulfonyl)ethyl)piperidine-1-carboxylate

HRID 1643465Notes

Reaction equation

HRID 1643465 reaction equation
FC1C(F)=C(F)C(F)=C(F)C=1O[S:5]([CH2:8][CH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]1)(=[O:7])=[O:6].[N:31]1([CH2:36][CH2:37][CH:38]2[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]2)[CH2:35][CH2:34][CH2:33][CH2:32]1.N12CCCN=C1CCCCC2.C(=O)(O)[O-].[Na+]>O1CCCC1.C(OCC)(=O)C>[N:31]1([CH2:36][CH2:37][CH:38]2[CH2:39][CH2:40][N:41]([S:5]([CH2:8][CH2:9][CH:10]3[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:11]3)(=[O:6])=[O:7])[CH2:42][CH2:43]2)[CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

7

Reactant 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2962934-[2-(Pyrrolidin-1-yl)ethyl]piperidineHCID 516892Sodium BicarbonateHCID 59367796HCID 59367796, compound

Product 1

HCID 59367815tert-Butyl 3-(2-(4-(2-(pyrrolidin-1-yl)ethyl)piperidin-1-ylsulfonyl)ethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 3-(2-(perfluorophenoxysulfonyl)ethyl)piperidine-1-carboxylate (0.5 g, 1.09 mmol) and 4-(2-pyrrolidinoethyl)piperidine (0.4 g, 2.18 mmol) were dissolved in tetrahydrofuran (10 ml), 1,8-diazabicyclo[5.4.0]undec-7-ene (0.5 ml, 3.27 mmol) was added under an inert gas and the mixture was refluxed for 2 h. Ethyl acetate and saturated sodium bicarbonate solution (20 ml of each) were added, the phases were separated and the aqueous phase was extracted with ethyl acetate (2×30 ml). The combined organic phases were washed with 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 ethyl acetate/methanol/ammonia (25% aq) (300:100:1). Yield: 0.32 g (64%)

Workup

  1. temperaturethe mixture was refluxed for 2 h
  2. customthe phases were separated
  3. extractionthe aqueous phase was extracted with ethyl acetate (2×30 ml)
  4. washThe combined organic phases were washed with saturated sodium chloride solution (20 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by column chromatography (silica gel) with ethyl acetate/methanol/ammonia (25% aq) (300:100:1)

Sources & evidence

ORD record
ord-779647ec967e4caaade07e048c0f48a4
Source dataset
uspto-grants-2012_02
Patent number
US08119805B2

Reaction notes

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