Potassium Carbonate → Tert-butyl 4-(((benzyloxy)carbonyl)(ethyl)amino)piperidine-1-carboxylate

HRID 1193413ノート

反応式

HRID 1193413 の反応式
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9](Cl)=[O:10])=[CH:3][CH:2]=1.C1(C)C=CC=CC=1.[CH2:19]([NH:21][CH:22]1[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]1)[CH3:20].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[CH2:7]([O:8][C:9]([N:21]([CH2:19][CH3:20])[CH:22]1[CH2:23][CH2:24][N:25]([C:28]([O:30][C:31]([CH3:33])([CH3:32])[CH3:34])=[O:29])[CH2:26][CH2:27]1)=[O:10])[C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 18374730tert-Butyl 4-(ethylamino)piperidine-1-carboxylateHCID 86663382Cbz-Cl toluene

生成物 1

HCID 18677722Tert-butyl 4-(((benzyloxy)carbonyl)(ethyl)amino)piperidine-1-carboxylate収率 63%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A 50% Cbz-Cl-toluene solution (20.87 ml, 61.40 mmol, 2.0 eq) was added dropwise at 0° C. to a mixture of tert-butyl 4-(ethylamino)piperidine-1-carboxylate (7.0 g, 30.70 mmol, 1.0 eq) and K2CO3 (12.71 g, 92.10 mmol, 3.0 eq) in DCM (100 ml) and the mixture was stirred for 14 hours at RT. The reaction mixture was diluted with DCM (200 ml), washed with water (100 ml) and sat. NaCl solution (100 ml), dried over sodium sulfate, concentrated under reduced pressure and purified by column chromatography (silica gel, 20% ethyl acetate in hexane). Yield: 63% (7.0 g, 19.33 mmol)

後処理

  1. washwashed with water (100 ml) and sat. NaCl solution (100 ml)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. custompurified by column chromatography (silica gel, 20% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-941621b5e21f455ab798c88bc2dc1798
出典データセット
uspto-grants-2014_03
特許番号
US08680159B2

反応ノート

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