Triethylamine → 1-(2,3-Dihydrobenzo[1,4]dioxine-2-carbonyl)-4-oxopiperidine-3-carboxylic acid methyl ester

HRID 453783

反応式

HRID 453783 の反応式
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1[C:11](Cl)=[O:12].[CH3:14][O:15][C:16]([CH:18]1[C:23](=[O:24])[CH2:22][CH2:21][NH:20][CH2:19]1)=[O:17].C(N(CC)CC)C.[OH-].[Na+]>CN(C=O)C.O>[CH3:14][O:15][C:16]([CH:18]1[C:23](=[O:24])[CH2:22][CH2:21][N:20]([C:11]([CH:2]2[O:1][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=3[O:4][CH2:3]2)=[O:12])[CH2:19]1)=[O:17]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 2724029Methyl 4-oxopiperidine-3-carboxylateHCID 27354472,3-Dihydro-1,4-benzodioxin-2-carbonyl chloride

生成物 1

HCID 667273031-(2,3-Dihydrobenzo[1,4]dioxine-2-carbonyl)-4-oxopiperidine-3-carboxylic acid methyl ester

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of 2,3-dihydrobenzo[1,4]dioxine-2-carbonyl chloride (2.0 g, 10.0 mmol) and 4-oxopiperidine-3-carboxylic acid methyl ester (2.14 g, 11.0 mmol) in DMF (5 ml) was added triethylamine (1.54 ml). The reaction mixture was stirred at RT for 5 h. The reaction mixture was taken up in water, made alkaline with aq NaOH and extracted with DCM to give 1-(2,3-dihydrobenzo[1,4]dioxine-2-carbonyl)-4-oxopiperidine-3-carboxylic acid methyl ester. A mixture of this product (0.2 g, 0.62 mmol), K2CO3 (0.17 g, 1.23 mmol) and methyl iodide (0.08 ml, 1.25 mmol) in acetone (20 ml) was irradiated in the microwave reactor at 56° C. for 90 min. Water was added and the reaction mixture extracted with EtOAc (3×5 ml). The combined organic phases were dried over Na2SO4, filtered and the filtrate was evaporated to give 1-(2,3-dihydrobenzo[1,4]dioxine-2-carbonyl)-3-methyl-4-oxopiperidine-3-carboxylic acid methyl ester, which was finally reduced with LiAlH4 in THF to afford the title compound.

後処理

  1. extractionextracted with DCM

出典と根拠

ORDレコード
ord-cda3852952fe48a89068598f8ac20820
出典データセット
uspto-grants-2013_07
特許番号
US08492549B2

関連ノート

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