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

HRID 43555노트

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HRID 43555 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

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온도
70 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-09f26b3182e34b3584bfbf2f2c7d972b
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536197B2

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