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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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(S)-(-)-N-Benzyl-1-phenylethylamine → methyl 3-{R}-[benzyl-({S}-1-phenyl-ethyl)-amino]-3-(1-boc-1,2,3,4-tetrahydro-quinolin-6-yl)-propionate

HRID 396724
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HRID 396724 반응식
[CH2:1]([NH:8][C@@H:9]([CH3:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[C:22]([N:29]1[C:38]2[C:33](=[CH:34][C:35]([CH:39]=[CH:40][C:41]([O:43][CH3:44])=[O:42])=[CH:36][CH:37]=2)[CH2:32][CH2:31][CH2:30]1)([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23]>O1CCCC1>[CH2:1]([N:8]([C@H:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:16])[C@@H:39]([C:35]1[CH:34]=[C:33]2[C:38](=[CH:37][CH:36]=1)[N:29]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:30][CH2:31][CH2:32]2)[CH2:40][C:41]([O:43][CH3:44])=[O:42])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
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참가 물질

5

반응물 3

HCID 1268085(S)-(-)-N-Benzyl-1-phenylethylamineHCID 54398523Methyl 3-(1-boc-1,2,3,4-tetrahydro-quinolin-6-yl)acrylateHCID 178418339Butyllithium

생성물 1

HCID 21354704methyl 3-{R}-[benzyl-({S}-1-phenyl-ethyl)-amino]-3-(1-boc-1,2,3,4-tetrahydro-quinolin-6-yl)-propionate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-70 °C

실험 절차

A solution of (S)-N-benzyl-α-methylbenzylamine (2.6 ml) in anhydrous tetrahydrofuran (50 ml), cooled to −70° C. and under nitrogen, was treated dropwise with a solution of butyllithium in hexanes (5 ml, 2.5M) over about 5 minutes to give a red solution. After stirring at −70° C. for a further 40 minutes the mixture was treated dropwise with a solution of methyl 3-(1-boc-1,2,3,4-tetrahydro-quinolin-6-yl)acrylate [2.0 g, Reference Example 7(d)] in tetrahydrofuran (20 ml) over about 10 minutes. Stirring was continued at low temperature for a further 20 minutes and then the reaction mixture was allowed to warm to room temperature. The mixture was partitioned between ether and water, the layers separated, and the organic layer washed with water then with brine, then dried and then evaporated. The residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and petrol (initially 1:9 and then 15:85, v/v) to give the title compound as a viscous, colourless oil, 1.5 g.

후처리

  1. customto give a red solution
  2. stirringStirring
  3. waitwas continued at low temperature for a further 20 minutes
  4. temperatureto warm to room temperature
  5. customThe mixture was partitioned between ether and water
  6. customthe layers separated
  7. washthe organic layer washed with water
  8. dry with materialwith brine, then dried
  9. customevaporated
  10. additionThe residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and petrol (initially 1:9

출처 및 근거

ORD 기록
ord-f504505246fc43f2b89bbd34262b5278
출처 데이터셋
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06608084B1

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