Ammonium formate → tert-Butyl cis(+/-)-4-amino-3-(benzyloxy)piperidine-1-carboxylate

HRID 43555ノート

反応式

HRID 43555 の反応式
C([O-])=O.[NH4+].C([NH:12][C@H:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][C@H:14]1[O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)C1C=CC=CC=1>CO.[Pd]>[NH2:12][C@H:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][C@H:14]1[O:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

参加物

5

反応物 2

HCID 2723923Ammonium formateHCID 86648570tert-Butyl cis(+/-)-4-(benzylamino)-3-(benzyloxy)piperidine-1-carboxylate

生成物 1

HCID 86648571tert-Butyl cis(+/-)-4-amino-3-(benzyloxy)piperidine-1-carboxylate収率 90.2%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

反応条件

温度
70 °C

実験手順

10% Pd/C (wet, 1.1 g) and ammonium formate (2.87 g, 46 mmol) were added to a solution of tert-butyl cis(±)-4-(benzylamino)-3-(benzyloxy)piperidine-1-carboxylate obtained in Example (90c) (4.84 g, 11.4 mmol) in methanol (30 mL) in a nitrogen atmosphere, and the mixture was stirred at 70° C. for 40 minutes. The reaction solution was filtered to remove the Pd/C. Following concentration under reduced pressure, a 1 N aqueous sodium hydroxide solution was added to the residue, followed by extraction with dichloromethane three times. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure, to obtain 3.15 g of the crude title compound as a colorless oily substance (94%).

後処理

  1. filtrationThe reaction solution was filtered
  2. customto remove the Pd/C
  3. concentrationconcentration under reduced pressure
  4. additiona 1 N aqueous sodium hydroxide solution was added to the residue
  5. extractionfollowed by extraction with dichloromethane three times
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-09f26b3182e34b3584bfbf2f2c7d972b
出典データセット
uspto-grants-2013_09
特許番号
US08536197B2

反応ノート

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