4-Benzylpiperidine → (S)-1-(4-benzyl-piperidin-1-yl)-3-[4-(6-fluoro-benzo[d]isoxazol-3-yl)-phenoxy]-propan-2-ol

HRID 852108

반응식

HRID 852108 반응식
[F:1][C:2]1[CH:21]=[CH:20][C:5]2[C:6]([C:9]3[CH:14]=[CH:13][C:12]([O:15][CH2:16][C@@H:17]4[CH2:19][O:18]4)=[CH:11][CH:10]=3)=[N:7][O:8][C:4]=2[CH:3]=1.[CH2:22]([CH:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C)C=O.C(O)C>[CH2:22]([CH:29]1[CH2:34][CH2:33][N:32]([CH2:19][C@H:17]([OH:18])[CH2:16][O:15][C:12]2[CH:13]=[CH:14][C:9]([C:6]3[C:5]4[CH:20]=[CH:21][C:2]([F:1])=[CH:3][C:4]=4[O:8][N:7]=3)=[CH:10][CH:11]=2)[CH2:31][CH2:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

참가 물질

5

반응물 2

HCID 317384-BenzylpiperidineHCID 11254641(S)-6-fluoro-3-(4-oxiranylmethoxy-phenyl)-benzo[d]isoxazole

생성물 1

HCID 9825507(S)-1-(4-benzyl-piperidin-1-yl)-3-[4-(6-fluoro-benzo[d]isoxazol-3-yl)-phenoxy]-propan-2-ol수율 70%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 6228Dimethylformamide용매

반응 조건

온도
85 °C

실험 절차

Combine (S)-6-fluoro-3-(4-oxiranylmethoxy-phenyl)-benzo[d]isoxazole (150 mg, 0.526 mmol) dissolved in dimethylformamide (˜2 mL) and add 0.13 M solution of 4-benzylpiperidine in ethanol (˜4 mL) and heat for 10 hours at 85° C. Concentrate and purify the reaction mixture by flash (silica) chromatography on a Water's Sep-Pak 5 g silica cartridge using a graded solvent mixture of dichloromethane to 10% methanol in dichloromethane to give the title compound (169.9 mg, 70% Yield). Purity by LC/MS=99%, [M+H]+=461.

후처리

  1. concentrationConcentrate
  2. custompurify the reaction mixture by flash (silica) chromatography on a Water'
  3. additiona graded solvent mixture of dichloromethane to 10% methanol in dichloromethane

출처 및 근거

ORD 기록
ord-099d0be113d54634872c63a608134850
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253165B2

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