Triethylamine → tert-Butyl 3-[4-(3-methoxypropyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-4-[4-(4-phenylpiperidine-1-carbonyl)phenyl]piperidine-1-carboxylate

HRID 1176517ノート

反応式

HRID 1176517 の反応式
[C:1]1([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Cl[C:21]([C:23]1[CH:28]=[CH:27][C:26]([CH:29]2[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31][CH:30]2[O:42][CH2:43][C:44]2[CH:45]=[CH:46][C:47]3[O:52][CH2:51][C:50](=[O:53])[N:49]([CH2:54][CH2:55][CH2:56][O:57][CH3:58])[C:48]=3[CH:59]=2)=[CH:25][CH:24]=1)=[O:22].C(=O)([O-])O.[Na+]>ClCCl>[CH3:58][O:57][CH2:56][CH2:55][CH2:54][N:49]1[C:48]2[CH:59]=[C:44]([CH2:43][O:42][CH:30]3[CH:29]([C:26]4[CH:27]=[CH:28][C:23]([C:21]([N:10]5[CH2:11][CH2:12][CH:7]([C:1]6[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=6)[CH2:8][CH2:9]5)=[O:22])=[CH:24][CH:25]=4)[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31]3)[CH:45]=[CH:46][C:47]=2[O:52][CH2:51][C:50]1=[O:53]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 698734-PhenylpiperidineHCID 516892Sodium BicarbonateHCID 86610013tert-Butyl 4-(4-chlorocarbonylphenyl)-3-[4-(3-methoxypropyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]piperidine-1-carboxylate

生成物 1

HCID 68504417tert-Butyl 3-[4-(3-methoxypropyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-4-[4-(4-phenylpiperidine-1-carbonyl)phenyl]piperidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

A solution of 0.122 g of 4-phenylpiperidine in 2 ml of dichloromethane is admixed with 0.101 ml of triethylamine. The reaction solution is cooled to 0° and a solution of tert-butyl 4-(4-chlorocarbonylphenyl)-3-[4-(3-methoxypropyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]piperidine-1-carboxylate in 4 ml of dichloromethane is added dropwise. The reaction mixture is stirred at 0° C. over 40 minutes and subsequently poured onto 25 ml of saturated sodium hydrogencarbonate solution. The mixture is extracted with 80 ml of dichloromethane, the phases are separated and the organic phase is washed with 40 ml each of water and brine, dried over sodium sulphate, filtered and concentrated. The residue is purified by means of flash chromatography (SiO2 60F). The title compound is obtained as a colourless oil. Rf=0.20 (3:1 EtOAc-heptane); Rt=5.44.

後処理

  1. temperatureThe reaction solution is cooled to 0°
  2. extractionThe mixture is extracted with 80 ml of dichloromethane
  3. customthe phases are separated
  4. washthe organic phase is washed with 40 ml each of water and brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue is purified by means of flash chromatography (SiO2 60F)

出典と根拠

ORDレコード
ord-515278d989914433bc354934a6cc69e0
出典データセット
uspto-grants-2010_11
特許番号
US07842688B2

反応ノート

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