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Sodium Sulfite → (3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-3-acetic acid

HRID 2186383
ノート
印刷プレビュー

反応式

HRID 2186383 の反応式
[Mn]([O-])(=O)(=O)=O.[K+].[O:7]=[C:8]([C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[C:34]([O:37][CH3:38])[CH:35]=2)[N:30]=[CH:29][CH:28]=1)[CH2:9][CH2:10][C@@H:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][C@@H:12]1[CH2:24][CH:25]=[O:26].S([O-])([O-])=[O:40].[Na+].[Na+]>O.CC(C)=O>[O:7]=[C:8]([C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[C:34]([O:37][CH3:38])[CH:35]=2)[N:30]=[CH:29][CH:28]=1)[CH2:9][CH2:10][C@@H:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[CH2:13][C@@H:12]1[CH2:24][C:25]([OH:40])=[O:26]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 24437Sodium SulfiteHCID 516875Potassium PermanganateHCID 86758164(3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-3-acetaldehyde

生成物 1

HCID 70176189(3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-3-acetic acid収率 59.5%

試薬・触媒・溶媒 2

HCID 180
Acetone
溶媒
2 回
HCID 962Water溶媒2 回

反応条件

温度
10 °C

実験手順

A solution of 0.85 g of potassium permanganate in 25 cm3 of water and 120 cm3 of acetone was added over approximately 1 hour, with stirring and at a temperature in the region of 25° C., to a solution of 1.2 g of (3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-3-acetaldehyde in 60 cm3 of acetone. The mixture was stirred for 3 hours at this same temperature and then cooled to approximately 10° C. A solution of 5 g of sodium sulfite in 200 cm3 of water was added to the reaction mixture and then the mixture obtained was filtered through celite. The acetone of the filtrate was evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C. and then the evaporation residue was taken up in 200 cm3 of water and washed with 200 cm3 of diethyl ether. The aqueous phase was separated by settling, acidified with citric acid in the solid state to a pH in the region of 3-4 and extracted with 200 cm3 of diethyl ether. The ethereal solution, separated by settling, was dried over magnesium sulfate, filtered, and evaporated under the above conditions. 0.74 g of (3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-3-acetic acid was obtained in the form of a yellow solid.

後処理

  1. customthe mixture obtained
  2. filtrationwas filtered through celite
  3. customThe acetone of the filtrate was evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C.
  4. washwashed with 200 cm3 of diethyl ether
  5. customThe aqueous phase was separated
  6. extractionextracted with 200 cm3 of diethyl ether
  7. customThe ethereal solution, separated
  8. dry with materialwas dried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated under the above conditions

出典と根拠

ORDレコード
ord-bc4c849f1d374474abdd7aa80bec5d83
出典データセット
uspto-grants-2002_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06403610B1

反応ノート

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