1-Amino-2-propanol → 1-((2-Hydroxyethyl)(methyl)amino)-3-(1-nitrocyclohexyl)propan-2-ol

HRID 446633ノート

反応式

HRID 446633 の反応式
[O:1]1[CH2:3][CH2:2]1.CC([CH2:7][NH2:8])O.[N+:9]([C:12]1([CH2:18][CH:19]2[CH2:21][O:20]2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)([O-:11])=[O:10]>>[OH:1][CH2:2][CH2:3][N:8]([CH3:7])[CH2:21][CH:19]([OH:20])[CH2:18][C:12]1([N+:9]([O-:11])=[O:10])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

参加物

4

反応物 3

HCID 41-Amino-2-propanol2 回HCID 6354Ethylene Oxide2 回HCID 583089362-((1-Nitrocyclohexyl)methyl)oxirane

生成物 1

HCID 583089381-((2-Hydroxyethyl)(methyl)amino)-3-(1-nitrocyclohexyl)propan-2-ol

実験手順

A one neck 100 mL round bottom flask equipped with a stir bar, condenser and nitrogen outlet is charged with 3.24 g (34.6% purity, 0.018 mols) of 24(1-nitrocyclohexyl)methyl)oxirane and 1.31 g (0.018 mols) of monomethylethanolamine. The reaction mixture is stirred at room temperature for 30 minutes followed by heating at 40° C. for 1.5 h. The yellow color oxirane turns to dark orange and the resulting product has high viscosity. GC of the reaction mixture after this time still shows the presence of the epoxide. At this point, 0.7 mL (0.65 g) of additional monomethylethanolamine is added and stirred for additional 1.5 h at 40° C. and overnight at room temperature. GC analysis of the resulting mixture shows the nitro epoxide (12) is fully consumed. At this point, the reaction is deemed complete. Compound (13), 1-((2-hydroxyethyl)(methyl)amino)-3-(1-nitrocyclohexyl)propan-2-ol was identified by LC/MS with [M+H]=261.17. The product mixture from the epoxy ring opening step is used as-is for the hydrogenation step.

後処理

  1. customA one neck 100 mL round bottom flask equipped with a stir bar, condenser and nitrogen outlet
  2. temperatureby heating at 40° C. for 1.5 h
  3. stirringstirred for additional 1.5 h at 40° C. and overnight at room temperature
  4. customis fully consumed

出典と根拠

ORDレコード
ord-5a74f53537ac4aa5b1de56d3a0bb78b3
出典データセット
uspto-grants-2013_07
特許番号
US08480800B2

反応ノート

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