Potassium Carbonate → 7-(((5-Bromo-4-chloro-2-nitrophenyl)amino)methyl)-3-neopentyl-1-oxa-3-azaspiro[4.5]decan-2-one

HRID 1423846ノート

反応式

HRID 1423846 の反応式
[Br:1][C:2]1[CH:7]=[C:6](F)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[Cl:12].[NH2:13][CH2:14][CH:15]1[CH2:30][CH2:29][CH2:28][C:17]2([O:21][C:20](=[O:22])[N:19]([CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:18]2)[CH2:16]1.C(=O)([O-])[O-].[K+].[K+]>CC#N>[Br:1][C:2]1[C:3]([Cl:12])=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH:13][CH2:14][CH:15]2[CH2:30][CH2:29][CH2:28][C:17]3([O:21][C:20](=[O:22])[N:19]([CH2:23][C:24]([CH3:26])([CH3:27])[CH3:25])[CH2:18]3)[CH2:16]2)[CH:7]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 104001051-Bromo-2-chloro-5-fluoro-4-nitrobenzeneHCID 711160567-(Aminomethyl)-3-neopentyl-1-oxa-3-azaspiro[4.5]decan-2-one

生成物 1

HCID 711160457-(((5-Bromo-4-chloro-2-nitrophenyl)amino)methyl)-3-neopentyl-1-oxa-3-azaspiro[4.5]decan-2-one収率 44.3%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A rt suspension of 1-bromo-2-chloro-5-fluoro-4-nitrobenzene (0.600 g, 2.36 mmol) in MeCN (8 mL) was treated with 7-(aminomethyl)-3-neopentyl-1-oxa-3-azaspiro[4.5]decan-2-one (0.400 g, 1.57 mmol) and potassium carbonate (0.543 g, 3.93 mmol). The reaction was stirred for 18 h, and the solids were filtered off and washed with EtOAc. The filtrate was concentrated and purified on a 40 g silica gel column (0-100% DCM/hexanes, 20 min gradient; 100% DCM, 15 min; 40 mL/min elution; 254 nm detection) to provide the title compound (0.340 g, 44% yield) as an orange solid. MS (m/z) 488.1, 490.1 (M+H+).

後処理

  1. filtrationthe solids were filtered off
  2. washwashed with EtOAc
  3. concentrationThe filtrate was concentrated
  4. custompurified on a 40 g silica gel column (0-100% DCM/hexanes, 20 min gradient; 100% DCM, 15 min; 40 mL/min elution; 254 nm detection)

出典と根拠

ORDレコード
ord-55a0e8fc57a746bf90ed4f2b1bb84814
出典データセット
uspto-grants-2015_01
特許番号
US08927585B2

反応ノート

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