(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

反応式

HRID 396724 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-70 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f504505246fc43f2b89bbd34262b5278
出典データセット
uspto-grants-2003_08
特許番号
US06608084B1

関連ノート

読み込み中…