Ethyl Acetate → HCID 67366133、化合物

HRID 1500320ノート

反応式

HRID 1500320 の反応式
[C:1](Cl)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C([N:19]1[CH2:24][CH2:23][C:22]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([N:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)[CH2:21][CH2:20]1)C1C=CC=CC=1.C(OCC)(=O)C>C(Cl)(Cl)Cl>[CH2:4]([O:3][C:1]([N:19]1[CH2:20][CH2:21][C:22]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([N:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)[CH2:23][CH2:24]1)=[O:2])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 10387Benzyl chloroformateHCID 67367347HCID 67367347、化合物

生成物 1

HCID 67366133HCID 67366133、化合物収率 29.3%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

60 g (3.5 eq) Cbz chloride were added dropwise to a solution of 33 g (1 eq) 1-benzyl-4-phenyl-4-(pyrrolidin-1-yl)piperidine in 330 ml chloroform over a period of 10 min and the reaction mixture obtained was stirred for 30 min at room temperature. The reaction course was monitored by thin-layer chromatography (ethyl acetate). Once the conversion was complete, the solvent was distilled off completely and the residue adjusted to a pH of ˜6 with 10% HCl solution and washed 3 times with 100 ml EtOAc. In an ice bath the aqueous solution was adjusted to a pH of ˜9 with NaOH solution and then extracted 3 times with 100 ml chloroform. The combined organic phases were dried with Na2SO4. Following removal of the solvent under reduced pressure, the residue was purified by column chromatography (silica gel; 20% EtOAc/heptane). 11 g (29%) of product were obtained in the form of a yellow solid.

後処理

  1. customthe reaction mixture obtained
  2. distillationthe solvent was distilled off completely
  3. washwashed 3 times with 100 ml EtOAc
  4. customIn an ice bath the aqueous solution was adjusted to a pH of ˜9 with NaOH solution
  5. extractionextracted 3 times with 100 ml chloroform
  6. dry with materialThe combined organic phases were dried with Na2SO4
  7. customremoval of the solvent under reduced pressure
  8. customthe residue was purified by column chromatography (silica gel; 20% EtOAc/heptane)

出典と根拠

ORDレコード
ord-3dac2108b91f41849af028febf8606dc
出典データセット
uspto-grants-2015_12
特許番号
US09206156B2

反応ノート

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