Ammonium formate → (S)-tert-butyl 4-aminoazepane-1-carboxylate

HRID 714535ノート

反応式

HRID 714535 の反応式
C1([C@H]([NH:9][C@H:10]2[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12][CH2:11]2)C)C=CC=CC=1.C([O-])=O.[NH4+]>CO.[OH-].[OH-].[Pd+2]>[NH2:9][C@H:10]1[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12][CH2:11]1

参加物

5

反応物 2

HCID 2723923Ammonium formateHCID 59027964tert-Butyl (S)-4-(((R)-1-phenylethyl)amino)azepane-1-carboxylate

生成物 1

HCID 32639843(S)-tert-butyl 4-aminoazepane-1-carboxylate収率 87.3%

試薬・触媒・溶媒 2

HCID 9942167Palladium hydroxide触媒HCID 887Methanol溶媒

実験手順

A suspension of Pd(OH)2/C (10%, 550 mg), tert-butyl (4S)-4-{[(1R)-1-phenylethyl]amino}azepane-1-carboxylate (5.5 g, 17.3 mmol) and HCOONH4 (3.3 g, 51.9 mmol) in MeOH (80 mL) was heated at reflux for 1.5 h. The reaction mixture was cooled to rt and filtered, the solvents of the filtrate were removed in vacuo. The residue was purified by column chromatography (gradient 0% to 10% MeOH in DCM) to give tert-butyl (4S)-4-aminoazepane-1-carboxylate (3.2 g, 87.3%).

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 h
  3. filtrationfiltered
  4. customthe solvents of the filtrate were removed in vacuo
  5. customThe residue was purified by column chromatography (gradient 0% to 10% MeOH in DCM)

出典と根拠

ORDレコード
ord-b0f5a0c581f44aa792e754e23df3ccd2
出典データセット
uspto-grants-2015_11
特許番号
US09187451B2

反応ノート

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