1-Bromo-2-Chloroethane → 1-Tert-butyl 3-ethyl 3-(2-chloroethyl)piperidine-1,3-dicarboxylate

HRID 1044352Notes

Reaction equation

HRID 1044352 reaction equation
C([N-]C(C)C)(C)C.[Li+].[N:9]1([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:14][CH2:13][CH2:12][CH:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:10]1.O1CCCC1.Br[CH2:33][CH2:34][Cl:35]>>[Cl:35][CH2:34][CH2:33][C:11]1([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:12][CH2:13][CH2:14][N:9]([C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[CH2:10]1

Participants

5

Reactant 4

HCID 78491-Bromo-2-ChloroethaneHCID 8028TetrahydrofuranHCID 3577271-Tert-butyl 3-ethyl piperidine-1,3-dicarboxylateHCID 2724682Lithium diisopropylamide

Product 1

HCID 667225341-Tert-butyl 3-ethyl 3-(2-chloroethyl)piperidine-1,3-dicarboxylate

Procedure

Lithium diisopropylamide (1.8 M in THF, 3.9 mL) was slowly added to a solution of 1-tert-butyl 3-ethyl piperidine-1,3-dicarboxylate (1.50 g, 0.00583 mol) in tetrahydrofuran (20 mL, 0.2 mol) at −78° C. and the mixture was stirred for about 1 hour during which the temperature was allowed to rise to about −50° C. 1-Bromo-2-chloro-ethane (0.75 mL, 0.0082 mol) was slowly added to the mixture and then the resulting mixture was allowed to warm to rt (room temperature). After stirring for 2 h, the reaction mixture was quenched with saturated NH4Cl and extracted with ethyl ether twice. The combined organic layers were dried and concentrated in-vacuo to afford the crude product, which was purified by CombiFlash eluting with hexane/EtOAc (max. EA 20%).

Workup

  1. customto rise to about −50° C
  2. stirringAfter stirring for 2 h
  3. customthe reaction mixture was quenched with saturated NH4Cl
  4. extractionextracted with ethyl ether twice
  5. customThe combined organic layers were dried
  6. concentrationconcentrated in-vacuo

Sources & evidence

ORD record
ord-9720694747c74d9e864524f444c0f689
Source dataset
uspto-grants-2013_10
Patent number
US08563570B2

Reaction notes

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