Triethylamine → cis-1-Tert-butyl 3-ethyl 4-methylpiperidine-1,3-dicarboxylate

HRID 931302ノート

反応式

HRID 931302 の反応式
C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.CC1CCNCC1C(OCC)=O.C(N(CC)CC)C.[CH3:35][CH:36]1[CH2:41][CH2:40][N:39]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:38][CH:37]1[C:49]([O:51][CH2:52][CH3:53])=[O:50]>ClCCl>[CH3:35][C@H:36]1[CH2:41][CH2:40][N:39]([C:42]([O:44][C:45]([CH3:48])([CH3:46])[CH3:47])=[O:43])[CH2:38][C@H:37]1[C:49]([O:51][CH2:52][CH3:53])=[O:50]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 13658603Ethyl 4-methylpiperidine-3-carboxylateHCID 707916011-Tert-butyl 3-ethyl 4-methylpiperidine-1,3-dicarboxylate

生成物 1

HCID 131735164cis-1-Tert-butyl 3-ethyl 4-methylpiperidine-1,3-dicarboxylate収率 83.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Di-tert-butyl dicarbonate (3.26 g, 15.20 mmol) was added to a solution of ethyl 4-methylpiperidine-3-carboxylate (2.0 g, 11.68 mmol) and triethylamine (3.9 mL, 28.05 mmol) in anhydrous dichloromethane (50 mL) at 0° C. The reaction mixture was stirred at room temperature for 18 h. The mixture partitioned between dichloromethane and water. The organics were dried over sodium sulfate, filtered and concentrated under reduced pressure to afford a mixture of the cis and trans diastereomers of 1-tert-butyl 3-ethyl 4-methylpiperidine-1,3-dicarboxylate (3.0 g). The crude material was purified via column chromatography (5-10% ethyl acetate in petroleum ether) to afford cis-1-tert-butyl 3-ethyl 4-methylpiperidine-1,3-dicarboxylate (2.5 g).

後処理

  1. customThe mixture partitioned between dichloromethane and water
  2. dry with materialThe organics were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto afford
  6. customThe crude material was purified via column chromatography (5-10% ethyl acetate in petroleum ether)

出典と根拠

ORDレコード
ord-4a634299e5f74e8d8bc683344d04df11
出典データセット
uspto-grants-2016_03
特許番号
US09296745B2

反応ノート

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