Ethanol → 4-[4-amino-3-(4-methyl-piperidin-1-yl)-phenyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

HRID 646896ノート

反応式

HRID 646896 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[C:16]([N:23]3[CH2:28][CH2:27][CH:26]([CH3:29])[CH2:25][CH2:24]3)[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+].CCO>[Fe].O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([N:23]3[CH2:28][CH2:27][CH:26]([CH3:29])[CH2:25][CH2:24]3)[CH:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 586385144-[3-(4-methyl-piperidin-1-yl)4-nitro-phenyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 586385524-[4-amino-3-(4-methyl-piperidin-1-yl)-phenyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester収率 53.8%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

A flask charged with 4-[3-(4-methyl-piperidin-1-yl)-4-nitro-phenyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (0.080 g, 0.20 mmol) (as prepared in the previous step), ammonium chloride (0.10 g, 2.0 mmol), iron powder (0.055 g, 10 mmol), EtOH (1 mL) and water (0.5 mL) was heated at 80° C. for 30 min. The reaction was filtered though Celite, concentrated and eluted from a 10-g SPE cartridge (silica) with 20% EtOAc/hexane to give 0.040 g (50%) of the title compound as a yellow oil. 1H-NMR (400 MHz, CDCl3): δ 7.08 (d, 1H), 6.97 (dd, 1H), 6.72 (d, 1H), 5.89 (m, 1H), 4.75 (br s, 2H), 4.08 (m, 2H), 3.63 (m, 2H), 3.12 (m, 2H), 2.62 (m, 2H), 2.50 (m, 2H), 1.78 (m, 2H), 1.52 (s, 9H), 1.38 (m, 3H), 1.00 (d, 3H).

後処理

  1. filtrationThe reaction was filtered though Celite
  2. concentrationconcentrated
  3. washeluted from a 10-g SPE cartridge (silica) with 20% EtOAc/hexane

出典と根拠

ORDレコード
ord-facc81d7b39b4120a62f83d3c39a707f
出典データセット
uspto-grants-2010_04
特許番号
US07705042B2

反応ノート

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