Water → (3R)-3-[(E)-2-[2-Benzyl-6-[(3R,4R)-3-hydroxy-4-methoxypyrrolidine-1-yl]-pyridyl]ethenyl]-3-quinuclidinol

HRID 1359379노트

반응식

HRID 1359379 반응식
[CH2:1]([C:8]1[C:13]([C:14]#[C:15][C@:16]2([OH:24])[CH:21]3[CH2:22][CH2:23][N:18]([CH2:19][CH2:20]3)[CH2:17]2)=[CH:12][CH:11]=[C:10]([N:25]2[CH2:29][C@@H:28]([O:30][CH3:31])[C@H:27]([OH:32])[CH2:26]2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C(OCC)C.O1CCCC1>[CH2:1]([C:8]1[C:13](/[CH:14]=[CH:15]/[C@:16]2([OH:24])[CH:21]3[CH2:20][CH2:19][N:18]([CH2:23][CH2:22]3)[CH2:17]2)=[CH:12][CH:11]=[C:10]([N:25]2[CH2:29][C@@H:28]([O:30][CH3:31])[C@H:27]([OH:32])[CH2:26]2)[N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 9845745(3R)-3-[2-Benzyl-6-[(3R,4R)-3-hydroxy-4-methoxypyrrolidine-1-yl]-3-pyridyl)ethynyl-3-quinuclidinolHCID 21226445Aluminium lithium hydride

생성물 1

HCID 69760518(3R)-3-[(E)-2-[2-Benzyl-6-[(3R,4R)-3-hydroxy-4-methoxypyrrolidine-1-yl]-pyridyl]ethenyl]-3-quinuclidinol수율 60.8%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

270 mg of (3R)-3-[2-benzyl-6-[(3R,4R)-3-hydroxy-4-methoxypyrrolidine-1-yl]-3-pyridyl]ethynyl-3-quinuclidinol (Example 10) was dissolved in 10 ml of ethyl ether. 300 mg of lithium aluminum hydride was added thereto, followed by heating under reflux for 6 hours. While stirring in an ice-bath, 0.3 ml of water, 0.3 ml of an aqueous 5N sodium hydroxide solution, 1 ml of water and 10 ml of tetrahydrofuran were added thereto. The mixture was filtered, and the filtrate was concentrated. The residue was then subjected to NH-silica gel column chromatography and eluted with 10% methanol/ethyl acetate, to give 165 mg of the target compound.

후처리

  1. temperatureby heating
  2. temperatureunder reflux for 6 hours
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. washeluted with 10% methanol/ethyl acetate

출처 및 근거

ORD 기록
ord-53b5fee81f404cb4887313bba151c811
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06599917B1

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