Triphenylphosphine → 4-Amino-1-(p-nitrobenzyloxycarbonyl)-piperidine

HRID 891714노트

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HRID 891714 반응식
[N:1]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[CH2:6][CH2:5]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C(#N)C>[NH2:1][CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[CH2:6][CH2:5]1

참가 물질

5

반응물 3

HCID 11776TriphenylphosphineHCID 62649Sodium sulfate decahydrateHCID 222427144-Azido-1-(p-nitrobenzyloxycarbonyl)piperidine

생성물 1

HCID 222428434-Amino-1-(p-nitrobenzyloxycarbonyl)-piperidine수율 91%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
70 °C

실험 절차

To a solution of 4-azido-1-(p-nitrobenzyloxycarbonyl)-piperidine (2.81 g, 9.17 mmol) (obtained as described in Reference Example 51(3)) in acetonitrile (84 ml) was added triphenylphosphine (2.53 g, 9.63 mmol), and the mixture was stirred in an oil bath (70° C.) for 3 hours. After checking the completion of the reaction, sodium sulfate decahydrate (3.10 g, 9.63 mmol) was added thereto and the reaction mixture was stirred for 3 hours. After checking the completion of the reaction, the reaction mixture was filtered and partitioned between methylene chloride and 0.1M aqueous hydrogen chloride solution. To the obtained aqueous layer were added methylene chloride and sodium hydrogencarbonate, and the aqueous layer was extracted with methylene chloride. The obtained organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was dried under reduced pressure to give 4-amino-1-(p-nitrobenzyloxycarbonyl)-piperidine (2.33 g, yield 91%) as pale yellow crystals.

후처리

  1. additionwas added
  2. stirringthe reaction mixture was stirred for 3 hours
  3. customthe completion of the reaction
  4. filtrationthe reaction mixture was filtered
  5. custompartitioned between methylene chloride and 0.1M aqueous hydrogen chloride solution
  6. additionTo the obtained aqueous layer were added methylene chloride and sodium hydrogencarbonate
  7. extractionthe aqueous layer was extracted with methylene chloride
  8. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was dried under reduced pressure

출처 및 근거

ORD 기록
ord-8169dd54444b4c67b565ae1632fba091
출처 데이터셋
uspto-grants-2006_02
특허 번호
US07001897B2

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