Benzyl chloroformate → 4-Amino-1-Cbz-piperidine-4-carboxylic acid

HRID 232011ノート

反応式

HRID 232011 の反応式
Br.[NH2:2][C:3]1([C:9]([OH:11])=[O:10])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.[C:12](Cl)([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13].[OH-].[Na+]>P([O-])(O)(O)=O.[K+].O.C1(C)C=CC=CC=1>[C:12]([N:6]1[CH2:7][CH2:8][C:3]([NH2:2])([C:9]([OH:11])=[O:10])[CH2:4][CH2:5]1)([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13]

参加物

7

反応物 3

HCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 200305764-Aminopiperidine-4-carboxylic acid hydrobromide

生成物 1

HCID 145370764-Amino-1-Cbz-piperidine-4-carboxylic acid収率 50.3%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1140Toluene溶媒HCID 516951Monobasic potassium phosphate溶媒

反応条件

温度
5 °C

実験手順

4-amino-4-carboxy-piperidine hydrobromide ([P. Jacobsen, K. Schaumburg, P. Krogsgaard-Larsen, Acta. Chem. Scandinavica B34, 319-326 (1980)]; 2.25 g, 10 mmoles) was dissolved in a solution of 18 ml potassium dihydrogen phosphate buffer (0.05 Molar potassium dihydrogen phosphate in 1N aqueous sodium hydroxide) and 6 ml of water. The solution was chilled with an ice-bath over an hour period during which solutions of carbobenzyloxy chloride (1.57 ml, 11 mmoles) in 3.0 ml of toluene and aqueous 1N sodium hydroxide were simultaneously added dropwise so as to maintain a pH of 7.0. The mixture was then stirred for one hour at 5° C., and for four additional hours at ambient temperature. The precipitate formed during the reaction was filtered and the filter cake washed with 3 (30 ml) portions of diethyl ether. The amorphous colorless solid was dried in vacuo affording 1.4 g of the title compound (50% yield). 1Hnmr (60 mHz; CF 3 CO2D) delta 2.0-2.7 (4H, broad m), 3.5-4.5 (4H, broad m), 5.28 (2H, s), 7.4 (5H, s).

後処理

  1. additionwere simultaneously added dropwise so as
  2. temperatureto maintain a pH of 7.0
  3. customat ambient temperature
  4. customThe precipitate formed during the reaction
  5. filtrationwas filtered
  6. washthe filter cake washed with 3 (30 ml) portions of diethyl ether
  7. customThe amorphous colorless solid was dried in vacuo

出典と根拠

ORDレコード
ord-772e28005b0d48ce8ceaa8f9ae470f88
出典データセット
uspto-grants-1989_07
特許番号
US04851388

反応ノート

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