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

HRID 48472ノート

反応式

HRID 48472 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 1.0 L round-bottom flask was charged with K2CO3 (29.2 g; 171 mmol), piperidine (50 g; 163 mmol), and a 1:1 mixture of THF/H2O (800 mL). A 150 mL addition funnel was placed on the flask and charged with CbzCl (29.2 g, 171 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 1 h. The reaction mixture was extracted with EtOAc (500 mL) and the organic layer was washed with water (500 mL), saturated NaCl (500 mL), dried (MgSO4), filtered and concentrated in vacuo. The crude material (49.3 g, 100% yield) was carried on without further purification.

後処理

  1. additionA 150 mL addition funnel
  2. temperatureThe reaction mixture was warmed to 20° C.
  3. extractionThe reaction mixture was extracted with EtOAc (500 mL)
  4. washthe organic layer was washed with water (500 mL), saturated NaCl (500 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-6b96d61185a74049914794dfc541726d
出典データセット
uspto-grants-2004_03
特許番号
US06703508B2

反応ノート

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