1-Bromo-2-Chloroethane → 1-Benzyl 4-methyl 4-(2-chloroethyl)piperidine-1,4-dicarboxylate

HRID 215942ノート

反応式

HRID 215942 の反応式
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[N:11]1([C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[CH2:16][CH2:15][CH:14]([C:17]([O:19][CH3:20])=[O:18])[CH2:13][CH2:12]1.Br[CH2:32][CH2:33][Cl:34]>O1CCCC1>[Cl:34][CH2:33][CH2:32][C:14]1([C:17]([O:19][CH3:20])=[O:18])[CH2:13][CH2:12][N:11]([C:21]([O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:22])[CH2:16][CH2:15]1

参加物

5

反応物 3

HCID 78491-Bromo-2-ChloroethaneHCID 15125441-Benzyl 4-methyl piperidine-1,4-dicarboxylateHCID 2733832Lithium Hexamethyldisilazide

生成物 1

HCID 588931841-Benzyl 4-methyl 4-(2-chloroethyl)piperidine-1,4-dicarboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

Lithium bis(trimethylsilyl)amide (LiHMDS) in THF (1.0 M, 7.2 mL, 0.0072 mol) was added to a solution of 1-benzyl 4-methyl piperidine-1,4-dicarboxylate (1.00 g, 0.00360 mol) in tetrahydrofuran (10.0 mL) at −78° C. The reaction mixture had been stirred at −78° C. for 1 hr, then 1-bromo-2-chloroethane (0.45 mL, 0.0054 mol) was slowly added to the mixture. The reaction mixture was allowed to warm to room temperature and stirred for 2 hrs. The reaction was quenched with saturated NH4Cl, extracted with ethyl acetate. The combined organic layers were dried over Na2SO4, filtered, concentrated. The residue was flash chromatographed (ethyl acetate in hexane: 20%) to afford 1-benzyl 4-methyl 4-(2-chloroethyl)piperidine-1,4-dicarboxylate.

後処理

  1. temperatureto warm to room temperature
  2. stirringstirred for 2 hrs
  3. customThe reaction was quenched with saturated NH4Cl
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed (ethyl acetate in hexane: 20%)

出典と根拠

ORDレコード
ord-a415cabdb7e14f55bef4e499903a0012
出典データセット
uspto-grants-2012_06
特許番号
US08193207B2

反応ノート

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