o-Xylyl bromide → 1-(1,1-Dimethylethyl) 4-methyl 4-[(2-methylphenyl)methyl]-1,4-piperidinedicarboxylate

HRID 443219ノート

反応式

HRID 443219 の反応式
[CH3:1][O:2][C:3](=[O:17])[CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.[Li+].CC([N-]C(C)C)C.[CH3:26][C:27]1[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=1[CH2:29]Br>C1COCC1>[CH3:1][O:2][C:3](=[O:17])[C:4]1([CH2:26][C:27]2[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=2[CH3:29])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])[CH2:6][CH2:5]1

参加物

5

反応物 3

HCID 6992o-Xylyl bromideHCID 3928701-N-Boc-4-Piperidinecarboxylic acid methyl esterHCID 2724682Lithium diisopropylamide

生成物 1

HCID 537754431-(1,1-Dimethylethyl) 4-methyl 4-[(2-methylphenyl)methyl]-1,4-piperidinedicarboxylate

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

To a solution of N-t-butoxycarbonyl isonipecotic acid methyl ester (10.1 g 41.8 mmol) in 140 ml of dry THF at -78° C. was added LDA (59 ml of a 1.0M solution in THF, 59 mmol) over 15 min. The resulting orange solution was stirred at -78° C. for 1 hr and then treated dropwise with 2-methylbenzyl bromide (6.80 ml, 50.7 mmol) and then allowed to warm slowly to room temperature over 16 hrs. The reaction was quenched with saturated aqueous NH4Cl, diluted with H2O, and extracted with EtOAc. The combined organic extracts were washed with brine, and concentrated in vacuo to an orange gum. Chromatography (SiO2, eluting with 20 to 30% EtOAc in hexanes) and evaporation of solvent in vacuo, afforded the product as a white solid.

後処理

  1. temperatureto warm slowly to room temperature over 16 hrs
  2. customThe reaction was quenched with saturated aqueous NH4Cl
  3. additiondiluted with H2O
  4. extractionextracted with EtOAc
  5. washThe combined organic extracts were washed with brine
  6. concentrationconcentrated in vacuo to an orange gum
  7. washChromatography (SiO2, eluting with 20 to 30% EtOAc in hexanes) and evaporation of solvent in vacuo

出典と根拠

ORDレコード
ord-74c6b88505534267ab9ca278e6c0be92
出典データセット
uspto-grants-1999_04
特許番号
US05891889

反応ノート

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