Potassium Permanganate → (3RS,4RS)-[4-(1-tert-butoxycarbonyl-3-naphthalen-2-ylmethoxy-piperidin-4-yl)-phenyl]-acetic acid

HRID 1858638

반응식

HRID 1858638 반응식
[Mn]([O-])(=O)(=O)=[O:2].[K+].[OH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH:17]2[O:29][CH2:30][C:31]2[CH:40]=[CH:39][C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH:32]=2)=[CH:12][CH:11]=1>O.C(O)(=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C1C=CC=CC=1>[C:25]([O:24][C:22]([N:19]1[CH2:20][CH2:21][CH:16]([C:13]2[CH:14]=[CH:15][C:10]([CH2:9][C:8]([OH:2])=[O:7])=[CH:11][CH:12]=2)[CH:17]([O:29][CH2:30][C:31]2[CH:40]=[CH:39][C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH:32]=2)[CH2:18]1)=[O:23])([CH3:28])([CH3:26])[CH3:27]

참가 물질

7

반응물 2

HCID 516875Potassium PermanganateHCID 53946013tert-butyl (3RS,4RS)-4-[4-(2-hydroxy-ethyl)-phenyl)-3-naphthalen-2-ylmethoxy-piperidine-1-carboxylate

생성물 1

HCID 22128103(3RS,4RS)-[4-(1-tert-butoxycarbonyl-3-naphthalen-2-ylmethoxy-piperidin-4-yl)-phenyl]-acetic acid수율 50.5%

시약·촉매·용매 4

HCID 67553Tetrabutylammonium Iodide촉매HCID 176Acetic Acid용매HCID 241Benzene용매HCID 962Water용매

실험 절차

6.95 g (44 mmol) of powdered potassium permanganate dissolved in a mixture of 100 ml of water and 100 ml of glacial acetic acid as well as 0.73 g (2 mmol) of tetrabutylammonium iodide were added to a solution of 5.0 g (10.83 mmol) of tert-butyl (3RS,4RS)-4-[4-(2-hydroxy-ethyl)-phenyl]-3-naphthalen-2-ylmethoxy-piperidine-1-carboxylate in 500 ml of benzene. The reaction mixture was stirred intensively for 48 hours. For the working-up, the phases were separated. The organic phase was washed with 100 ml of saturated sodium thiosulphate solution. The aqueous phase was decolorized by the addition of saturated sodium thiosulphate solution and subsequently extracted twice with 100 ml of ethyl acetate and 100 ml of methylene chloride each time. The organic phases were combined, dried over sodium sulphate and evaporated under reduced pressure. For purification, the crude material was chromatographed on silica gel using a 9:1 mixture of methylene chloride and methanol as the eluent after the column had previously been prepared with a 90:10:0.1 mixture of methylene chloride, methanol and ammonia. There were obtained 2.6 g (50% of theory) of (3RS,4RS)-[4-(1-tert-butoxycarbonyl-3-naphthalen-2-ylmethoxy-piperidin-4-yl)-phenyl]-acetic acid as a colourless, amorphous solid; MS: 476 (M+H)+.

후처리

  1. customthe phases were separated
  2. washThe organic phase was washed with 100 ml of saturated sodium thiosulphate solution
  3. additionThe aqueous phase was decolorized by the addition of saturated sodium thiosulphate solution
  4. extractionsubsequently extracted twice with 100 ml of ethyl acetate and 100 ml of methylene chloride each time
  5. dry with materialdried over sodium sulphate
  6. customevaporated under reduced pressure
  7. customFor purification
  8. customthe crude material was chromatographed on silica gel using
  9. additiona 9:1 mixture of methylene chloride and methanol as the eluent after the column
  10. customhad previously been prepared with a 90:10:0.1 mixture of methylene chloride, methanol and ammonia

출처 및 근거

ORD 기록
ord-af35f4e067ed4ec9a0051be52a295a80
출처 데이터셋
uspto-grants-2000_11
특허 번호
US06150526

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