Methyl chloroformate → Tert-butyl 4-{1-[(methoxycarbonyl)oxy]-3-(6-methylpyridin-2-yl)prop-2-yn-1-yl}piperidine-1-carboxylate

HRID 1895991ノート

反応式

HRID 1895991 の反応式
[OH:1][CH:2]([CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1)[C:3]#[C:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[N:6]=1.C(N(CC)CC)C.Cl[C:33]([O:35][CH3:36])=[O:34]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:36][O:35][C:33]([O:1][CH:2]([CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1)[C:3]#[C:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[N:6]=1)=[O:34]

参加物

6

反応物 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 68725592Tert-butyl 4-[1-hydroxy-3-(6-methylpyridin-2-yl)prop-2-ynyl]piperidine-1-carboxylate

生成物 1

HCID 68725060Tert-butyl 4-{1-[(methoxycarbonyl)oxy]-3-(6-methylpyridin-2-yl)prop-2-yn-1-yl}piperidine-1-carboxylate

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of the Compound of Example 39 (50 mg, 0.15 mmol), triethylamine (65 μL, 0.45 mmol) and 4-dimethylaminopyridine (10 mg, 0.07 mmol) in 3 mL of CH2Cl2 cooled at 0-5° C., methyl chloroformate (23 μL, 0.30 mmol) was added dropwise. The reaction mixture was stirred at r.t. overnight. Afterwards, it was evaporated to dryness and purified by automated flash liquid chromatography (Horizon™-Biotage) eluting with Petroleum Ether-EtOAc 8:2 affording the title product (0.28 g) as a brown oil.

後処理

  1. customAfterwards, it was evaporated to dryness
  2. custompurified by automated flash liquid chromatography (Horizon™-Biotage)
  3. washeluting with Petroleum Ether-EtOAc 8:2 affording the title product (0.28 g) as a brown oil

出典と根拠

ORDレコード
ord-17c29791f4a243a9bda0fb8fea311f67
出典データセット
uspto-grants-2013_08
特許番号
US08518916B2

反応ノート

読み込み中…