Potassium Carbonate → 3-Methoxynaltrexone

HRID 1051165노트

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HRID 1051165 반응식
[OH:1][C@:2]12[C@H:11]3[CH2:12][C:13]4[C:18]5[C@@:7]1([CH2:8][CH2:9][NH:10]3)[C@@H:6]([O:19][C:17]=5[C:16]([O:20][CH3:21])=[CH:15][CH:14]=4)[C:5](=[O:22])[CH2:4][CH2:3]2.C([O-])([O-])=O.[K+].[K+].[CH:29]1([CH2:32]Br)[CH2:31][CH2:30]1>CC#N>[CH:29]1([CH2:32][N:10]2[CH2:9][CH2:8][C@@:7]34[C:18]5[C:13]6[CH2:12][C@@H:11]2[C@:2]3([OH:1])[CH2:3][CH2:4][C:5](=[O:22])[C@@H:6]4[O:19][C:17]=5[C:16]([O:20][CH3:21])=[CH:15][CH:14]=6)[CH2:31][CH2:30]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 5489120Noroxycodone

생성물 1

HCID 54876953-Methoxynaltrexone

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a suspension of Compound 3 (9.5 g, 31.5 mmol) in 80 mL of CH3CN was added K2CO3 (10.9 g, 79.0 mmol) portionwise followed by cyclopropylmethyl bromide (3.97 mL, 41.0 mmol) dropwise via syringe. The suspension was heated at reflux for 18 h. LC-MS showed a single peak corresponding to the desired product (Tr=0.830 min, M+H=356). The mixture was cooled to ambient temperature and the solid was filtered off and washed with CH3CN. The filtrate was concentrated and the golden yellow residue was diluted with CH2Cl2 and H2O. The layers were separated and the aqueous was further extracted with CH2Cl2. The combined organics were washed with brine, dried over MgSO4, filtered, and concentrated to provide 9.76 g (87%) of Compound 4 as a white foam that turned to a light yellow oily foam overnight. LC/MS, m/z=356.2 [M+H]+ (Calc: 356.43).

후처리

  1. temperatureThe suspension was heated
  2. temperatureat reflux for 18 h

출처 및 근거

ORD 기록
ord-3ed5e977b17045a7bb16c802cfe2e1a9
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09388162B2

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