Ammonium Chloride → (4-Amino-3-methoxy-benzyl)-benzyl-carbamic acid tert-butyl ester

HRID 1019753ノート

反応式

HRID 1019753 の反応式
[C:1]([O:5][C:6](=[O:27])[N:7]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[C:11]([O:18][CH3:19])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[NH4+].[Cl-]>CO.[Zn]>[C:1]([O:5][C:6](=[O:27])[N:7]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([O:18][CH3:19])[CH:10]=1)[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 2

HCID 25517Ammonium ChlorideHCID 67256007Benzyl-(3-methoxy-4-nitro-benzyl)-carbamic acid tert-butyl ester

生成物 1

HCID 21034184(4-Amino-3-methoxy-benzyl)-benzyl-carbamic acid tert-butyl ester収率 85.3%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 887Methanol溶媒

反応条件

温度
60 °C

実験手順

To a solution of benzyl-(3-methoxy-4-nitro-benzyl)-carbamic acid tert-butyl ester (1.2 g, 3.22 mmol) in methanol (24 mL) was added a saturated aqueous solution of NH4Cl (24 mL) and zinc powder (1.05 g 16.11 mmol). The reaction was heated to 60° C. for 2 hours then the reaction mass was cooled to room temperature and filtered through celite. The solvents were removed under reduced pressure then the residue was partitioned between EtOAc (24 mL) and water (24 mL). The separated aqueous layer was extracted with EtOAc (12 ml), and then the combined organic extracts were washed with water (24 mL), brine (24 mL), dried (Na2SO4) and concentrated under reduced pressure to give the title compound (0.94 g, 85%).

後処理

  1. temperaturethe reaction mass was cooled to room temperature
  2. filtrationfiltered through celite
  3. customThe solvents were removed under reduced pressure
  4. customthe residue was partitioned between EtOAc (24 mL) and water (24 mL)
  5. extractionThe separated aqueous layer was extracted with EtOAc (12 ml)
  6. washthe combined organic extracts were washed with water (24 mL), brine (24 mL)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-9ffaba7b644846b1b1568756e4d7b2a6
出典データセット
uspto-grants-2014_05
特許番号
US08716287B2

反応ノート

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