1-Benzyl-4-piperidone → 1-Benzyl-4-hydroxy-4-(6-methoxynaphth-2-yl)piperidine

HRID 380544노트

반응식

HRID 380544 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[CH:8][CH:7]=[C:6]2Br.C([Li])(C)(C)C.[CH2:19]([N:26]1[CH2:31][CH2:30][C:29](=[O:32])[CH2:28][CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O1CCCC1>[CH2:19]([N:26]1[CH2:31][CH2:30][C:29]([OH:32])([C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=3)[CH:9]=2)[CH2:28][CH2:27]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

참가 물질

5

반응물 3

HCID 192201-Benzyl-4-piperidoneHCID 130258361-bromo-7-methoxyNaphthaleneHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 183652491-Benzyl-4-hydroxy-4-(6-methoxynaphth-2-yl)piperidine수율 63%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 5.0 gm (21.1 mMol) 6-methoxy-4-bromonaphthalene in 120 mL tetrahydrofuran was first cooled to −78° C. and then 27.3 mL (46.4 mMol) tert-butyllithium (1.7 M in pentane) were added and the resulting solution stirred for about 1.5 hours. At this point a solution of 4.1 mL (22.1 mMol) 1-benzylpiperidin-4-one in 30 mL tetrahydrofuran was added and the reaction mixture was allowed to warm gradually to room temperature. After 3 hours the reaction was quenched by the addition of 2 N sodium hydroxide. The resulting mixture was extracted with diethyl ether. The organic extracts were combined, washed with saturated aqueous sodium chloride, and concentrated under reduced pressure. The residue was subjected to flash silica gel chromatography, eluting with dichloromethane containing from 0 to 2% methanol. Fractions containing product were combined and concentrated under reduced pressure. The residue was crystallized from ethyl acetate to provide 4.62 gm (63%) of the desired compound as a white solid.

후처리

  1. customAfter 3 hours the reaction was quenched by the addition of 2 N sodium hydroxide
  2. extractionThe resulting mixture was extracted with diethyl ether
  3. washwashed with saturated aqueous sodium chloride
  4. concentrationconcentrated under reduced pressure
  5. washeluting with dichloromethane containing from 0 to 2% methanol
  6. additionFractions containing product
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was crystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-73fd92d80172435da08ae102ff585a18
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06303627B1

반응 노트

불러오는 중…