Benzyl chloroformate → 1-(Phenylmethyl) (3R)-1,3-piperidinedicarboxylate

HRID 1020059ノート

反応式

HRID 1020059 の反応式
[NH:1]1[CH2:6][CH2:5][CH2:4][C@@H:3]([C:7]([OH:9])=[O:8])[CH2:2]1.C(=O)(O)[O-].[Na+].Cl[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]>C1COCC1.O>[CH2:19]([O:18][C:16]([N:1]1[CH2:6][CH2:5][CH2:4][C@@H:3]([C:7]([OH:9])=[O:8])[CH2:2]1)=[O:17])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

6

反応物 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 1796510(-)-Nipecotic acid

生成物 1

HCID 7365381-(Phenylmethyl) (3R)-1,3-piperidinedicarboxylate収率 36%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A solution of (R)-piperidine-3-carboxylic acid (XXVII) (5.0 g, 39 mmol) in a mixture of 50 ml of THF and 20 ml of water was cooled to 0° C. and sodium bicarbonate (6.5 g, 77.4 mmol) and benzyl chloroformate (8.0 g, 46.4 mmol) were added simultaneously. The reaction mixture was stirred at 0° C. for 30 min and at room temperature for 3 hours and concentrated under reduced pressure. The remaining aqueous phase was extracted with ethyl ether to remove excess of benzyl chloroformate, then it was acidified with 1 M HCl solution to pH 6 followed by extraction with ethyl acetate. The organic layer was separated, dried over sodium sulfate and evaporated to provide (R)-piperidine-1,3-dicarboxylic acid 1-benzyl ester (XXVIII) (3.7 g, 36%).

後処理

  1. concentrationconcentrated under reduced pressure
  2. extractionThe remaining aqueous phase was extracted with ethyl ether
  3. customto remove excess of benzyl chloroformate
  4. extractionfollowed by extraction with ethyl acetate
  5. customThe organic layer was separated
  6. dry with materialdried over sodium sulfate
  7. customevaporated

出典と根拠

ORDレコード
ord-35ed7565ed0f4c14948f8dd1f09fdc2a
出典データセット
uspto-grants-2014_05
特許番号
US08716296B2

反応ノート

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