Toluene → 1-((Benzyloxy)carbonyl)-3-methylpiperidine-2-carboxylic acid

HRID 60882

反応式

HRID 60882 の反応式
Cl.[CH3:2][CH:3]1[CH2:8][CH2:7][CH2:6][NH:5][CH:4]1[C:9]([OH:11])=[O:10].Cl[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14].C1(C)C=CC=CC=1>[OH-].[Na+].C1COCC1>[CH2:16]([O:15][C:13]([N:5]1[CH2:6][CH2:7][CH2:8][CH:3]([CH3:2])[CH:4]1[C:9]([OH:11])=[O:10])=[O:14])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

5

反応物 3

HCID 1140TolueneHCID 10387Benzyl chloroformateHCID 696193093-Methylpiperidine-2-carboxylic acid hydrochloride

生成物 1

HCID 666248731-((Benzyloxy)carbonyl)-3-methylpiperidine-2-carboxylic acid

試薬・触媒・溶媒 1

HCID 20445995Sodium hydroxide tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

3-Methylpiperidine-2-carboxylic acid hydrochloride (28.5 g, 31.6 mmol) was dissolved in (1:1) 2 M NaOH/THF (600 mL) and cooled to 0° C. Benzyl chloroformate (31.57 ml, 222 mmol) was then added dropwise and the reaction was stirred overnight. Toluene was then added and organic layer discarded to remove unreacted chloroformate. The aqueous layer was made acidic (pH=2) with conc. HCl and the product was extracted with EtOAc, dried (MgSO4), and concentrated in vacuo to give a crude residue which was used without further purification (41.6 g, 94.5%). 1H NMR (CDCl3, 400 MHz) δ 7.40-7.37 (m, 5H), 5.19 (m, 2H), 4.95-4.72 (m, 1H), 4.14-4.03 (m, 1H), 3.36-3.25 (m, 1H), 1.93-1.53 (m, 5H), 1.20-1.05 (m, 3H).

後処理

  1. customto remove unreacted chloroformate
  2. extractionthe product was extracted with EtOAc
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-0409c044ad724af4a04c943f9ed3440b
出典データセット
uspto-grants-2016_09
特許番号
US09440982B2

関連ノート

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