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Methyl iodide → HCID 86646601、化合物

HRID 1963238
ノート
印刷プレビュー

反応式

HRID 1963238 の反応式
[NH:1]1[C:5]([CH:6]2[CH2:11][CH:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:9][CH2:8][N:7]2[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])=[N:4][N:3]=[N:2]1.IC.[C:29]([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:29][N:3]1[N:2]=[N:1][C:5]([CH:6]2[CH2:11][CH:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:9][CH2:8][N:7]2[C:17]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:18])=[N:4]1.[CH3:29][N:4]1[C:5]([CH:6]2[CH2:11][CH:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:9][CH2:8][N:7]2[C:17]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:18])=[N:1][N:2]=[N:3]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178469255HCID 178469255、化合物

生成物 2

HCID 66734713HCID 66734713、化合物収率 32%HCID 86646601HCID 86646601、化合物収率 51%

試薬・触媒・溶媒 1

HCID 180Acetone
溶媒

実験手順

1-Benzyl 4-ethyl 2-(1H-tetrazol-5-yl)piperidine-1,4-dicarboxylate (3.45 g, 9.60 mmol) was dissolved in acetone (20 mL) and iodomethane (2.99 mL, 48.00 mmol) and K2CO3 (3.98 g, 28.80 mmol) were added. The mixture was stirred at room temperature for 3 h. The reaction mixture was partitioned between water and EtOAc. The aqueous layer was extracted twice with EtOAc and the combined organic phase was washed with water and evaporated. The crude product was purified on a 100 g Biotage column with heptane/EtOAc 88/12-0/100 over 12 column volumes (CV). 1-Benzyl 4-ethyl 2-(2-methyl-2H-tetrazol-5-yl)piperidine-1,4-dicarboxylate (1.84 g, 51%) and 1-benzyl 4-ethyl 2-(1-methyl-1H-tetrazol-5-yl)piperidine-1,4-dicarboxylate (1.14 g, 32%) were isolated. 2-Methyl-isomer: 1H NMR (400 MHz, cdcl3) δ 1.15 (t, 3H), 1.75-1.87 (m, 1H), 2.02-2.11 (m, 1H), 2.27-2.37 (m, 1H), 2.66-2.78 (m, 2H), 3.55-3.65 (m, 1H), 3.75-3.86 (m, 1H), 3.90-3.99 (m, 1H), 4.01-4.09 (m, 1H), 4.25 (s, 3H), 5.13 (q, 2H), 5.55-5.62 (m, 1H), 7.25-7.38 (m, 5H). MS m/z 374 (M+H)+. 3-Methyl-isomer: MS m/z 374 (M+H)+

後処理

  1. customThe reaction mixture was partitioned between water and EtOAc
  2. extractionThe aqueous layer was extracted twice with EtOAc
  3. washthe combined organic phase was washed with water
  4. customevaporated
  5. customThe crude product was purified on a 100 g Biotage column with heptane/EtOAc 88/12-0/100 over 12 column volumes (CV)

出典と根拠

ORDレコード
ord-693130be051b4bf4bbf326f17a010ea6
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08415378B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート