1,3-Dibromopropane → Diethyl 2,2-pyrrolidinedicarboxylate

HRID 421205

反応式

HRID 421205 の反応式
[O-]CC.[Na+].[NH2:5][CH:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8].Br[CH2:18][CH2:19][CH2:20]Br>C(O)C.Cl>[NH:5]1[CH2:20][CH2:19][CH2:18][C:6]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:12]([O:14][CH2:15][CH3:16])=[O:13]

参加物

6

反応物 3

HCID 80011,3-DibromopropaneHCID 81272Propanedioic acid, 2-amino-, 1,3-diethyl esterHCID 2723922Sodium ethoxide

生成物 1

HCID 12524347Diethyl 2,2-pyrrolidinedicarboxylate

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 702Ethanol溶媒2 回

実験手順

To a solution of sodium ethoxide (5.14 g) in absolute ethanol (75 mL) at 0° C. under a nitrogen atmosphere, a solution of diethyl aminomalonate (hydrochloride salt, 8 g) in absolute ethanol (75 mL) was slowly added. A yellow suspension was obtained at the end of the addition. 1,3-dibromo propane (7.7 mL) was then added and the resulting mixture was stirred at reflux temperature for 5 hours. The mixture was allowed to cool down to rt, then ethanol was removed in vacuo to give a yellow solid. This was dissolved in HCl (1M solution, 20 mL) and then washed with ethyl ether (2×50 mL). Phases were separated and the aqueous phase was brought to pH=9 by adding NaOH (1M solution). It was then extracted with ethyl ether (3×50 mL) and washed with brine (20 mL). The organic phase was dried and concentrated in vacuo to give the desired compound (2.35 g) as yellow oil.

後処理

  1. customA yellow suspension was obtained at the end of the addition
  2. temperatureat reflux temperature for 5 hours
  3. customethanol was removed in vacuo
  4. customto give a yellow solid
  5. washwashed with ethyl ether (2×50 mL)
  6. customPhases were separated
  7. additionby adding NaOH (1M solution)
  8. extractionIt was then extracted with ethyl ether (3×50 mL)
  9. washwashed with brine (20 mL)
  10. customThe organic phase was dried
  11. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-4fa3026d12d047dbbd6729e9420bc257
出典データセット
uspto-grants-2012_01
特許番号
US08097618B2

関連ノート

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