Acetic Acid → tert-Butyl 4-(1-(4-aminonaphthalen-1-yloxy)propan-2-yl)pyridin-2-ylcarbamate

HRID 2069061ノート

反応式

HRID 2069061 の反応式
[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([O:14][CH2:15][CH:16]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH:19]=2)[CH3:17])=[CH:6][CH:5]=1)([O-])=O.CC(O)=O.CCOC(C)=O.[H][H]>CO.[Pt]>[NH2:1][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([O:14][CH2:15][CH:16]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH:19]=2)[CH3:17])=[CH:6][CH:5]=1

参加物

7

反応物 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 58532579tert-Butyl 4-(1-(4-nitronaphthalen-1-yloxy)propan-2-yl)pyridin-2-ylcarbamateHCID 178418361HCID 178418361、化合物

生成物 1

HCID 58532582tert-Butyl 4-(1-(4-aminonaphthalen-1-yloxy)propan-2-yl)pyridin-2-ylcarbamate収率 107.6%

試薬・触媒・溶媒 2

HCID 23939Platinum触媒HCID 887Methanol溶媒

実験手順

A solution of the nitroarene (54) (0.61 g, 1.441 mmol) in a mixture of MeOH (20.0 mL), AcOH (5.0 mL) and EtOAc (10.0 mL) was passed through a Thales H-Cube (1.0 mL·min−1, 45° C., 55 mm, 10% Pt/C Cat-Cart, full hydrogen mode). The solvent was evaporated in vacuo and the residue was partitioned between saturated aqueous NaHCO3 solution and EtOAc. The organic layer was washed with water and brine and then dried (MgSO4) and evaporated in vacuo to furnish the title compound (55) (0.61 g, 97%): m/z 394 (M+H)+ (ES+).

後処理

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was partitioned between saturated aqueous NaHCO3 solution and EtOAc
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo

出典と根拠

ORDレコード
ord-e0487f5068474bd182e0553a7081f50e
出典データセット
uspto-grants-2012_10
特許番号
US08299073B2

反応ノート

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