(3R)-3-ethynyl-1-azabicyclo[2.2.2]octan-3-ol → (3r)-3-({2-Benzyl-6-[(3r,4s)-3-Hydroxy-4-Methoxypyrrolidin-1-Yl]pyridin-3-Yl}ethynyl)-1-Azabicyclo[2.2.2]octan-3-Ol

HRID 1359342노트

반응식

HRID 1359342 반응식
[CH2:1]([C:8]1[C:13](I)=[CH:12][CH:11]=[C:10]([N:15]2[CH2:19][C@H:18]([O:20][CH3:21])[C@H:17]([OH:22])[CH2:16]2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]([C@:25]1([OH:33])[CH:30]2[CH2:31][CH2:32][N:27]([CH2:28][CH2:29]2)[CH2:26]1)#[CH:24]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(N(CC)CC)C>[CH2:1]([C:8]1[C:13]([C:24]#[C:23][C@:25]2([OH:33])[CH:30]3[CH2:31][CH2:32][N:27]([CH2:28][CH2:29]3)[CH2:26]2)=[CH:12][CH:11]=[C:10]([N:15]2[CH2:19][C@H:18]([O:20][CH3:21])[C@H:17]([OH:22])[CH2:16]2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 2

HCID 946095(3R)-3-ethynyl-1-azabicyclo[2.2.2]octan-3-olHCID 693629412-Benzyl-3-iodo-6-[(3R,4S)-3-hydroxy-4-methoxypyrrolidin-1-yl]pyridine

생성물 1

HCID 44450555(3r)-3-({2-Benzyl-6-[(3r,4s)-3-Hydroxy-4-Methoxypyrrolidin-1-Yl]pyridin-3-Yl}ethynyl)-1-Azabicyclo[2.2.2]octan-3-Ol수율 82.3%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8471Triethylamine용매

실험 절차

A mixture of 4.6 g of 2-benzyl-3-iodo-6-[(3R,4S)-3-hydroxy-4-methoxypyrrolidine-1-yl]pyridine, 1.7 g of (3R)-3-ethynyl-3-quinuclidinol, 130 mg of tetrakis(triphenylphosphine)palladium(0), 110 mg of cuprous iodide and 3.1 ml of triethylamine was stirred for 5 hours at room temperature in a nitrogen atmosphere. The reaction solution was extracted with aqueous dilute ammonia-ethyl acetate, and the organic phase was washed with water and brine, dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to NH-silica gel column chromatography using 0-5% methanol/ethyl acetate, to give 4.0 g of the target compound.

후처리

  1. extractionThe reaction solution was extracted with aqueous dilute ammonia-ethyl acetate
  2. washthe organic phase was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-dcd8505704b14cbaa065da048afd2aab
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06599917B1

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