Ammonium Acetate → {1-[4-Amino-1-(4-methoxy-phenyl)-cyclohexyl]-propyl}carbamic acid benzyl ester

HRID 45196ノート

反応式

HRID 45196 の反応式
[CH2:1]([O:8][C:9](=[O:29])[NH:10][CH:11]([C:14]1([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]1)[CH2:12][CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:36].[Na+]>CO>[CH2:1]([O:8][C:9](=[O:29])[NH:10][CH:11]([C:14]1([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[CH2:19][CH2:18][CH:17]([NH2:36])[CH2:16][CH2:15]1)[CH2:12][CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 58380957{1-[1-(4-Methoxy-phenyl)-4-oxo-cyclohexyl]-propyl}-carbamic acid benzyl ester

生成物 1

HCID 58380970{1-[4-Amino-1-(4-methoxy-phenyl)-cyclohexyl]-propyl}carbamic acid benzyl ester収率 74.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

200 mg (0.51 mmol) of the ketone (97) were dissolved in 1.5 mL of absolute methanol, then 390 mg (5.06 mmol) of ammonium acetate and 31.8 mg (0.51 mmol) of sodium cyanoborohydride were added, and the mixture was stirred at room temperature for 2 h. The reaction mixture was evaporated, the residue dissolved in 50 mL of 1N aqueous sodium hydroxide and extracted twice with 100 mL of dichloromethane. The combined organic layer was dried over magnesium sulphate, filtered, and evaporated to give 150 mg of the title compound 98 in a purity sufficient to be used directly in the next step. Rt=1.18 min (Method 19). Detected mass: 397.3 (M+H+).

後処理

  1. customThe reaction mixture was evaporated
  2. dissolutionthe residue dissolved in 50 mL of 1N aqueous sodium hydroxide
  3. extractionextracted twice with 100 mL of dichloromethane
  4. dry with materialThe combined organic layer was dried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated

出典と根拠

ORDレコード
ord-5ea78663d3ae494da452edd7ff86087b
出典データセット
uspto-grants-2013_09
特許番号
US08541449B2

反応ノート

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