Trimethylsilyldiazomethane → 1-tert-Butyl 3-methyl piperidine-1,3-dicarboxylate

HRID 30405

반응식

HRID 30405 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]([OH:16])=[O:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:17][Si](C=[N+]=[N-])(C)C>CO.C1(C)C=CC=CC=1>[CH3:17][O:15][C:14]([CH:10]1[CH2:11][CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9]1)=[O:16]

참가 물질

4

반응물 2

HCID 167693TrimethylsilyldiazomethaneHCID 27356471-((Tert-butoxy)carbonyl)piperidine-3-carboxylic acid

생성물 1

HCID 235906521-tert-Butyl 3-methyl piperidine-1,3-dicarboxylate수율 83.7%

시약·촉매·용매 1

HCID 21867641Toluene methanol용매

실험 절차

To a room temperature solution of piperidine-1,3-dicarboxylic acid-1-tert-butyl ester (5.00 g, 21.81 mmol) in 20% MeOH/toluene (100 ml) was added 14.18 ml of (trimethylsilyl)diazomethane (2.0 M, 28.35 mmol) dropwise and the reaction was monitored by TLC until completion and then concentrated under reduced pressure to yield 4.44 g (83.7%) of piperidine-1,3-dicarboxylic acid 1-tert-butyl ester-3-methyl ester (Intermediate 53). 1H NMR (400 MHz, CDCl3) δ ppm 1.4 (s, 9 H), 1.6 (d, J=3.4 Hz, 1 H), 1.6 (m, 1 H), 1.7 (m, 1 H), 2.0 (m, 1 H), 2.4 (m, 1 H), 2.8 (m, 1 H), 3.0 (s, 1 H), 3.7 (s, 3 H), 3.9 (d, J13.2 Hz, 1 H), 4.1 (s, 1 H).

후처리

  1. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-92547feaf7f44f27b6965639d1b5618b
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423054B2

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