1-Aminomethyl-5-methoxy-3-phenyl-3,4-dihydronaphthalene hydrochloride → [1R,3S] 1-aminomethyl-5-methoxy-3-phenyl-1,2,3,4-tetrahydronaphthalene hydrochloride

HRID 982095노트

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HRID 982095 반응식
[ClH:1].[NH2:2][CH2:3][C:4]1[C:13]2[C:8](=[C:9]([O:14][CH3:15])[CH:10]=[CH:11][CH:12]=2)[CH2:7][CH:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:5]=1.[H][H]>C(O)C.[Pd]>[ClH:1].[NH2:2][CH2:3][C@H:4]1[C:13]2[C:8](=[C:9]([O:14][CH3:15])[CH:10]=[CH:11][CH:12]=2)[CH2:7][C@@H:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:5]1

참가 물질

5

반응물 2

HCID 200690961-Aminomethyl-5-methoxy-3-phenyl-3,4-dihydronaphthalene hydrochlorideHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 67931190[1R,3S] 1-aminomethyl-5-methoxy-3-phenyl-1,2,3,4-tetrahydronaphthalene hydrochloride수율 79%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

To 0.22 g (0.73 mmol) of 1-aminomethyl-5-methoxy-3-phenyl-3,4-dihydronaphthalene hydrochloride, from Step 2, of Example 2, in 5 mL of absolute ethanol, was added 0.05 g of 10% palladium supported on carbon. The reaction mixture was sealed under a blanket of hydrogen and stirred overnight at ambient temperature. The reaction mixture was flushed with nitrogen before it was filtered through Celite filter aid and washed with 15 mL of absolute ethanol and 15 mL of methylene chloride. The filtrate was concentrated to give 0.16 g (79% yield) of [1R,3S] 1-aminomethyl-5-methoxy-3-phenyl-1,2,3,4-tetrahydronaphthalene hydrochloride, m. p. 235°-237° C.; 1H NMR (d6-DMSO) δ2.15-2.25 (m, 2H), 2.5-2.65 (m, 1H), 2.8-2.95 (m, 2H), 3.0-3.1 (m, 1H), 3.1-3.4 (m, 1H), 3.45-3.5 (m, 1H), 3.72 (s, 3H), 6.43 (d, 1H), 6.62 (d, 1H), 6.94 (t, 1H), 7.2-7.3 (m, 1H), 7.35-7.45 (m, 4H).

후처리

  1. customThe reaction mixture was flushed with nitrogen before it
  2. filtrationwas filtered through Celite
  3. filtrationfilter aid
  4. washwashed with 15 mL of absolute ethanol and 15 mL of methylene chloride
  5. concentrationThe filtrate was concentrated

출처 및 근거

ORD 기록
ord-950cda6b1d824e0cb8855d6439aae712
출처 데이터셋
uspto-grants-1991_02
특허 번호
US04994486

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