Piperidine → (S)-1-Benzyl 3-ethyl piperidine-1,3-dicarboxylate

HRID 720036ノート

反応式

HRID 720036 の反応式
[C:1]([O-:4])([O-:3])=O.[K+].[K+].[NH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[C:13](Cl)([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14].[CH2:24]1COC[CH2:25]1.O>>[CH2:24]([O:3][C:1]([C@H:9]1[CH2:10][CH2:11][CH2:12][N:7]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:8]1)=[O:4])[CH3:25]

参加物

5

反応物 4

HCID 8082PiperidineHCID 10387Benzyl chloroformate2 回HCID 11430Potassium CarbonateHCID 21881883Oxolane--water (1/1)

生成物 1

HCID 40634406(S)-1-Benzyl 3-ethyl piperidine-1,3-dicarboxylate収率 100%

反応条件

温度
0 °C

実験手順

A 250 mL round-bottom flask was charged with K2CO3 (13.5 g, 97.6 mmol), piperidine (10 g, 32.5 mmol), and a 1:1 mixture of THF/H2O (100 mL). A 50 mL addition funnel was placed on the flask and charged with CbzCl (6.67 g, 39.0 mmol). The flask was cooled to 0° C. and then CbzCl was added dropwise over 5 minutes. The reaction mixture was warmed to 20° C. and stirred for 12 h. The reaction mixture was extracted with EtOAc (250 mL) and the organic layer was washed with saturated NaCl (250 mL), dried (MgSO4), filtered and concentrated in vacuo. The crude material (9.5 g, 100% yield) was carried on without further purification.

後処理

  1. additionA 50 mL addition funnel
  2. temperatureThe reaction mixture was warmed to 20° C.
  3. extractionThe reaction mixture was extracted with EtOAc (250 mL)
  4. washthe organic layer was washed with saturated NaCl (250 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-296690d55ed54cb588bebbcaf1061682
出典データセット
uspto-grants-2006_11
特許番号
US07132551B2

反応ノート

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