Water → HCID 66959269, 화합물

HRID 1244458

반응식

HRID 1244458 반응식
[CH:1]1([C@@:6]([OH:15])([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)[C:7]([OH:9])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.O[C@H:29]1[CH:34]2[CH2:35][CH2:36][N:31]([CH2:32][CH2:33]2)[CH2:30]1.O>CN(C=O)C>[N:31]12[CH2:36][CH2:35][CH:34]([CH2:33][CH2:32]1)[C@H:29]([O:8][C:7](=[O:9])[C@:6]([CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)([OH:15])[C:10]1[S:11][CH:12]=[CH:13][CH:14]=1)[CH2:30]2

참가 물질

6

반응물 4

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 7364113-Quinuclidinol, (+)-HCID 66608566HCID 66608566, 화합물

생성물 1

HCID 66959269HCID 66959269, 화합물수율 47.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

510 mg (0.00225 mol) of (2S)-2-Cyclopentyl-2-hydroxy-2-thien-2-ylacetic acid (obtained by hydrolysis of Intermediate I-15a) were dissolved in 7 ml of DMF. This solution was stirred at room temperature and 638 mg (0.00393 mol) of 1,1′-carbonyldiimidazol were added in several portions. After 4.5 h the reaction mixture was cooled to 0° C. and 315 mg (0.00248 mol) of (3S)-3-hydroxy-1-azabicyclo[2.2.2]octane and 83 mg (0.0021 mol) of HNa (60% dispersion in mineral oil) were added thereto. After stirring 112 h at room temperature the reaction mixture was treated with water and extracted three times with diethyl ether. The organic layers were combined, washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography (eluent CHCl6/MeOH 15:1) to obtain 360 mg (47.6%) of the title product as an oil, structure confirmed by 1H-RMN.

후처리

  1. temperatureAfter 4.5 h the reaction mixture was cooled to 0° C.
  2. stirringAfter stirring 112 h at room temperature the reaction mixture
  3. extractionextracted three times with diethyl ether
  4. washwashed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was purified by silica gel column chromatography (eluent CHCl6/MeOH 15:1)

출처 및 근거

ORD 기록
ord-3142c1281e72492da7d0dbc4526923ab
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07122558B2

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