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

HRID 2365991

반응식

HRID 2365991 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  1. extractionextracted with DCM

출처 및 근거

ORD 기록
ord-5a27a753e42d415d8a7c41086ab4ffbf
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697723B2

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